Synthesis of solid-phase bound sulfonate esters

Article abstract of DOI:10.1081/SCC-100105328

p-Pivaloyloxybenzenesulfonyl and methylsulfonyl residues were used as linkers to attach secondary alcohols to Wang resin and to Merrifield resin, respectively. p-Pivaloyloxybenzenesulfonates of alcohols were deprotected at the phenolic group and coupled with Wang resin by Mitsunobu reaction whereas mesylates were lithiated at the methyl group and subsequently connected with chloromethyl residues of Merrifield resin.

Full text of DOI:10.1081/SCC-100105328

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SYNTHESIS OF SOLID-PHASE BOUND SULFONATE
ESTERS
Bartlomiej Furman a , Robert Łysek a , Łukasz Matyjasek a , Wojciech Wojtkielewicz a &
Marek Chmielewski b
a Institute of Organic Chemistry of the Polish Academy of Sciences , Kasprzaka 44/52,
Warsaw, 01 224, Poland
b Institute of Organic Chemistry of the Polish Academy of Sciences , Kasprzaka 44/52,
Warsaw, 01 224, Poland
Published online: 15 Aug 2006.
To cite this article: Bartlomiej Furman , Robert Łysek , Łukasz Matyjasek , Wojciech Wojtkielewicz & Marek Chmielewski
(2001) SYNTHESIS OF SOLID-PHASE BOUND SULFONATE ESTERS, Synthetic Communications: An International Journal for
Rapid Communication of Synthetic Organic Chemistry, 31:18, 2795-2802, DOI: 10.1081/SCC-100105328
To link to this article: http://dx.doi.org/10.1081/SCC-100105328
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SYNTHETIC COMMUNICATIONS, 31(18), 2795–2802 (2001)
SYNTHESIS OF SOLID-PHASE
BOUND SULFONATE ESTERS
Bartlomiej Furman, Robert Lysek, Lukasz Matyjasek,
Wojciech Wojtkielewicz, and Marek Chmielewski*
Institute of Organic Chemistry of the Polish Academy
of Sciences, Kasprzaka 44/52, 01 224 Warsaw, Poland
ABSTRACT
p-Pivaloyloxybenzenesulfonyl and methylsulfonyl residues
were used as linkers to attach secondary alcohols to Wang
resin and to Merrifield resin, respectively. p-Pivaloyloxy-
benzenesulfonates of alcohols were deprotected at the pheno-
lic group and coupled with Wang resin by Mitsunobu reaction
whereas mesylates were lithiated at the methyl group and sub-
sequently connected with chloromethyl residues of Merrifield
resin.
Synthesis of small molecules on polymers is a rapidly growing area of
organic chemistry owing to the emergence of a combinatorial approach to
drug discovery programmes.1 The sulfonyl functional group plays a parti-
cularly important role in such syntheses2 due to its ability to bind molecules
to the polymer support, and at the same time making a cleavage of the target
compound feasible by a variety of methods.2–4 As a part of our program
*Corresponding author.
2795
Copyright & 2001 by Marcel Dekker, Inc.
www.dekker.com

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FURMAN ET AL.
aimed at development of new polymer bound synthetic methodologies, we
directed attention to the use of sulfonate linkers.
To the best of our knowledge, a polymer-bound sulfonylation of sec-
ondary alcohols has not been reported, so far. In this paper we present the
methodologies based on p-pivaloyloxybenzenesulfonate esters and methane-
sulfonate esters. The first one employs sulfonates available from secondary
alcohols and p-pivaloyloxybenzenesulfonyl chloride (1).6 After deprotec-
tion, the phenolic group of the sulfonate ester is suitable to be attached
to a polymer, possessing a terminal hydroxyl, by the Mitsunobu procedure.
It should be noted that the preparation of 16 from sodium p-hydroxy-
benzenesulfonate is easier than the preparation of its 4-acetoxy congener.7
The second methodology uses readily available methanesulfonyl esters
which after transformation into a-lithio sulfonate esters can easily be
linked to the Merrifield chloromethyl resin.
In order to demonstrate the usefulness of the both approaches we
selected three secondary alcohols 2–4 to bind them to the commercially
available Wang resin via the p-oxybenzenesulfonyl linker and to the
Merrifield chloromethyl resin via lithium anions of respective mesylates.
The successful formation of solid-phase bound sulfonate ester was proved
by liberation of the starting alcohol from the resin.
Scheme 1.
Alcohols 2–4 (compound 3 was used as a commercially available
trans–cis mixture in a proportion ca. 4:1, respectively) were sulfonylated
with 1 in the presence of pyridine to provide respective sulfonates 5–7 in
good yields (93–94%). The pivaloyl residue was removed by treatment of
compounds 5–7 with sodium methoxide in methanol to afford correspond-
ing phenols 8–10. Formation of 8–10 using p-hydroxybenzenesulfonyl chlor-
ide8 according to the Takahashi et al. method9 gave a low yield due to the
selfsulfonylation reaction.

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2797
Phenols 8–10 were attached to the Wang resin by the Mitsunobu
reaction9–11 to give the corresponding polymer-supported alcohols 11–13
in yields 75, 79 and 94%, respectively, deduced by elemental analysis of
sulfur. Alcohols 2–4 can be easily cleaved from the polymer by reduction
of 11–13 with LiAlH4 to provide an additional proof of bounding the R0
substituent to the polymer.
Mesyl esters 14–16 were prepared from the alcohols 2–4 by standard
procedures. Formation of respective a-lithio sulfonates was performed accor-
ding to the Musicki and Widlanski procedure.5 An alkylation of lithiated
sulfonates with the commercially available Merrifield resin proceeded
smoothly to afford respective resin-linked compounds 17–19. The yield of
alkylation: 73, 75and 79%, respectively, was deduced, by the sulfur analysis
as above. The resin-bound sulfonate esters 17–19 can be cleaved, with LiAlH4
as above, to provide 2–4 in 90, 69, 80% yield, respectively.
In summary, we demonstrated that the sulfonyl linkers can be easily
attached to secondary alcohols by sulfonylation and to terminals of the
Wang resin by the Mitsunobu reaction, or else to the Merrifield resin
by alkylation with the lithiated mesyl esters. It should be pointed out
that the commercially available chlorosulfonylated polystyrene PS-TsCl
(Argonaut Technologies, 1.59 mmol/g) reacts easily with primary alcohols,12
whereas with the secondary alcohols 2–4 it affords corresponding sulfonates
in 13, 15and 5% yield only (estimated after cleavage from the resin by
Table 1.
11
12
17
18
13
19

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FURMAN ET AL.
LiAlH4 reduction). It should be noticed that both methodologies proposed
by us do not leave any free sulfonyl-acid group on the resin, contrary to the
sulfonylation of alcohols performed with the use of chlorosulfonylated
resins. It can be critical if the reaction carried out on a resin employed
acid sensitive reactants.
EXPERIMENTAL
Melting points were determined on a Kofler hot-stage apparatus
1
with microscope and are uncorrected. H NMR spectra were obtained on
Brucker Avance 500 and Varian Gemini AC-200 spectrometers for solution
in CDCl3. Chemical shifts are expressed in ppm downfield from the signal
for Me4Si. IR spectra were recorded on a Perkin Elmer FT-IR Spectrum
2000 spectrophotometer. Mass spectra were determined with an AMD 604
Inectra GmbH spectrometer. Optical rotations were measured using a
JASCO P 3010 polarimeter at ambient temperature. All reactions were
performed under atmospheres of dry N2 in anhydrous solvents distilled
from the following desiccants: CH2Cl2 and pyridine from CaH2, and THF
from Na-benzophenone. Wang and Merrifield resins were reagent grade and
used as purchased without further purification. Column chromatography
was performed on Merck Silica gel (230–400 mesh).
p-Pivaloyloxybenzenesulfonyl chloride was obtained from commer-
cially available sodium salt of p-hydroxybenzenesulfonic acid according
to the procedure described in Ref. 6. Compound 3 was used as a commer-
cially available trans–cis mixture in a ratio of ca. 4:1, respectively. Therefore
compounds 6, 9 and 15 are the mixtures of trans and cis isomers.
Synthesis of compounds 5–7. Compounds 5–7 were obtained from the
respective alcohols 2–4 (10 mmol) by treatment with p-pivaloyloxybenzene-
sulfonyl chloride (14 mmol) in pyridine solution (20 mL) at 0ꢀC, overnight.
The standard work up followed by chromatographical purification afforded
compounds 5–7 in about 93% yield.
1,2:5,6-Di-O-isopropylidene-3-O-( p-pivaloyloxybenzenesulfonyl)-
a-D-glucofuranose (5). Compound 5 was obtained from 2 according to the
procedure described above (92%). Colorless solid; mp. 81–83ꢀC; ½aŠD22-70.1
(c 0.6, CH2Cl2); IR (CHCl3): 844, 1105, 1375, 1757 cmÀ1 1H NMR
;
(200 MHz, CDCl3): d 1.17, 1.22 (2s, 6H, 5,6-O-isoprop), 1.37 (s, 9H, Piv),
1.32, 1.49 (2s, 6H, 1,2-O-isoprop), 3.88–4.08 (m, 4H, H-4,5,6a,6b), 4.80 (m,
1H, H-3), 4.86 (d, 1H, J 3.7 Hz, H-2), 5.94 (d, 1H, J 3.7 Hz, H-1), 7.22–7.30,
7.84–8.02 (2m, 4H, phenyl); MS (EI, HR) m/z: (MþH)þ calcd for
C23H33O10S: 501.17944. Found: 501.17804; Anal. Calcd for C23H32O10S
(500.58): C, 55.19; H, 6.44; S, 6.41. Found: C, 55.19; H, 6.57; S, 6.40.

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2799
4-tert-Butylcyclohexyl p-pivaloyloxybenzenesulfonate (6). Compound 6
was obtained from 3 according to the procedure described above (90%).
1
Colorless solid; IR (CHCl3): 827, 1109, 1366, 1756, 2960 cmÀ1; H NMR
(200 MHz, CDCl3) selected signals: d 0.81 (s, 9H, tert-butyl), 0.84 (s, 9H,
tert-butyl), 1.37 (s, Piv), 4.30–4.46, 4.76–4.80 (2m, 1H of cis and trans, H-1),
7.21–7.30, 7.90–7.98 (2m, 4H, phenyl); Anal. Calcd for C21H32O5S (396.559):
C, 63.61; H, 8.13; S, 8.09. Found: C, 63.66; H, 8.30; S, 7.88.
5-Cholesten-3b-yl( p-pivaloyloxybenzenesulfonate)(7).Compound7was
obtained from 4 according to the procedure described above (91%).
Colorless solid; mp. 117–119ꢀC; ½aŠD22-32.3 (c 0.4, CH2Cl2); IR (CHCl3):
934, 1109, 1163, 1365, 1757, 2952 cmÀ1 1H NMR (200 MHz, CDCl3)
;
selected signals: d 1.35(s, 9H, Piv), 4.27–4.44 (m, 1H, H-3), 5.32 (m, 1H,
H-6), 7.22–7.29, 7.90–7.97 (2m, 4H, phenyl); MS (LSIMS, HR) m/z:
(M þ Na)þ calcd for C38H58O5SNa: 649.39026. Found: 649.39011.
Synthesis of compounds 8–10. Compounds 8–10 were obtained from
the respective p-pivaloyloxybenzenesulfonate esters 5–7 (6 mmol) by treat-
ment with NaOMe (10 mmol) in MeOH solution (10 mL) at r.t. After 6 h the
reactions were neutralised with solid carbon dioxide, and extracted with
CH2Cl2. The extracts were washed with water, dried (MgSO4) and evapo-
rated to give the crude products 8–10. Chromatographic purification
afforded compounds 8–10 in about 90% yield.
3-O-( p-Hydroxybenzenesulfonyl)-1,2:5,6-di-O-isopropylidene-a-
D-glucofuranose (8). Compound 8 was obtained from 5 according to the
procedure described above (92%). Yellow solid; mp. 139–143ꢀC; [a]D
-
;
22
66.6 (c 1.0, CH2Cl2); IR (CHCl3): 844, 1076, 1167, 1374, 3247 cmÀ1
1H NMR (200 MHz, CDCl3): d 1.17, 1.22 (2s, 6H, 5,6-O-isoprop), 1.32,
1.49 (2s, 6H, 1,2-O-isoprop), 1.75(br s, 1H, -OH), 3.88 À4.11 (m, 4H, H-
4,5,6a,6b), 4.77 (m, 1H, H-3), 4.83 (d, 1H, J 3.6 Hz, H-2), 5.93 (d, 1H, J
3.6 Hz, H-1), 6.90–6.98, 7.79–7.88 (2m, 4H, phenyl); MS (LSIMS, HR) m/z:
(M þ Na)þ calcd for C18H24O9SNa: 439.10387. Found: 439.10611; Anal.
Calcd for C18H24O9S (416.46): C, 51.92; H, 5.81; S, 7.7. Found: C, 51.93;
H, 6.01; S, 7.53.
4-tert-Butylcyclohexyl p-hydroxybenzenesulfonate (9). Compound was
obtained from 6 according to the procedure described above (90%). White
1
solid; IR (CHCl3): 942, 1165, 1349, 1590, 2957 cmÀ1; H NMR (200 MHz,
CDCl3) selected signals: d 0.81 (s, 9H, tert-butyl), 0.83 (s, 9H, tert-butyl),
4.24–4.41, 4.72–4.75(2m, 2H, H-1), 6.91–6.99, 7.75–7.83 (2m, 4H, phenyl);
MS (EI, HR) m/z: Mþ calcd for C16H24O4S: 312.13953. Found: 312.98758;
Anal. Calcd for C16H24O4S (312.44): C, 61.51; H, 7.74. Found: C, 60.86;
H, 7.90.
5-Cholesten-3b-yl ( p-hydroxybenzenesulfonate) (10). Compound 10
was obtained from 7 according to the procedure described above (91%).

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FURMAN ET AL.
Colorless solid; mp. 110–114ꢀC with decomposition; ½aŠ2D2-35.2 (c 1.0,
CH2Cl2); IR (CHCl3): 867, 937, 1166, 1351, 1590, 3247 cmÀ1 1H NMR
;
(200 MHz, CDCl3) selected signals: d 4.20–4.38 (m, 1H, H-3), 5.29 (m, 1H,
H-6), 6.91–6.99, 7.75–7.83 (2m, 4H, phenyl); Anal. Calcd for C33H50O4S
(542.84): C, 73.02; H, 9.28; S 5.91. Found: C, 72.95; H, 9.57; S 5.83.
General procedure for the preparation of polymer bound sulfonate esters
11–13 via Mitsunobu procedure: To a suspension of Wang resin (0.5g,
0.54 mmol) in CH2Cl2 (8 mL) were added phenol 8 (0.91 g, 2.2 mmol)
and PPh3 (0.58 g, 2.2 mmol). The mixture, stirred and then cooled to
0ꢀC, was treated with DEAD (diethyl azodicarboxylate) (0.38 g, 2.2 mmol)
over 10 min and then the reaction was allowed to warm to r.t. The mixture
was stirred for 24 h, then filtered and washed (2 ꢁ 10 mL each) CH2Cl2,
MeOH, THF, 2:1 THF-water, THF, MeOH, CH2Cl2 and Et2O then dried
for 6 h under vacuum to give the resin 11. IR (KBr): 834, 1073, 1373 cmÀ1
.
Elemental analysis indicating 2.0% S, gives 75% yield. Cleavage by LiAlH4
(10 equiv.) in THF at 60ꢀC provided alcohol 2 (80% yield).
Resin 12. IR (KBr): 950, 1165, 1365 cmÀ1. Elemental analysis indicat-
ing 2.2% S, gives 79% yield. The yield determinated by LiAlH4 cleavage
was 70%.
Resin 13. IR (KBr): 862, 936, 1164, 1364 cmÀ1. Elemental analysis
indicating 2.1% S, gives 94% yield. The yield determinated by LiAlH4
cleavage was 87%.
Synthesis of compounds 14–16. Compounds 14–16 were obtained from
the respective alcohols 2–4 (10 mmol) by treatment with methylsulfonyl
chloride (14 mmol) in pyridine solution (20 mL) at 0ꢀC, overnight. The
standard work up followed by chromatographic purification afforded com-
pounds 14–16 in about 85% yield.
1,2:5,6-Di-O-isopropylidene-3-O-methylsulfonyl-a-D-glucofuranose (14).
Compound 14 was obtained from 2 according to the procedure described
above (81%). Colorless crystals; mp. 82–83.5ꢀC (from Et2O-hexane);
½aŠ2D2-46.2 (c 0.7, CH2Cl2); IR (CHCl3): 844, 1077, 1179, 1372, 2992 cmÀ1
;
[lit.,13 mp. 80–82ꢀC; ½aŠD22-49.0 (c 1.0, CHCl3)].
4-tert-Butylcyclohexyl methylsulfonate (15). Compound 15 was
obtained from 3 according to the procedure described above (85%).
1
Colorless crystals; IR (CHCl3): 926, 1171, 1332, 1352, 2959 cmÀ1; H NMR
(200 MHz, CDCl3) selected signals: d 0.85(s, 9H, tert-butyl), 0.87 (s, 9H,
tert-butyl), 3.0 (s, 3H, Ms), 3.01 (s, 3H, Ms), 4.48–4.65(m, 1H, H-1),
4.95–5.02 (m, 1H, H-1); (lit.14 provides data of pure trans and cis isomers).
5-Cholesten-3b-yl methylsulfonate (16). Compound 16 was obtained
from 4 according to the procedure described above (85%). Colorless
crystals; mp 120–122ꢀC (from hexane); ½aŠD22-31.5( c 0.78, CH2Cl2); IR
(CHCl3): 931, 1179, 1333, 1359, 2952 cmÀ1; (lit.,15 mp. 115–116ꢀC).

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General procedure for the alkylation of Merrifield resin with a-lithio
sulfonate esters: To a solution of 14 (0.81 g, 2.4 mmol) in THF (12 mL)
and DMPU (4 mL) was added dropwise at À70ꢀC the solution of butyl-
lithium in hexane (2.5M, 1 mL, 2.5mmol). After 15min, the Merrifield resin
(0.5g, 0.6 mmol), was added in one portion. The stirring was continued at
the same temperature for 20 min and then at À25ꢀC for 5h. The reaction
was quenched at À25ꢀC by an addition of 5mL of MeOH, then filtered
and washed (2 ꢁ 20 mL each) with MeOH, 2:1 THF-water, water, 2:1
THF-water, THF, MeOH, CH2Cl2 and Et2O then dried for 6 h under
vacuum to give the resin 17. IR (KBr): 1075, 1169, 1216, 1373 cmÀ1
.
Elemental analysis indicating 2.06% S, gives 73% yield. The yield determi-
nated by LiAlH4 cleavage was 90%.
Resin 18. IR (KBr): 904, 942, 1166, 1365cm À1. Elemental analysis
indicating 2.3% S, gives 75% yield. The yield determinated by LiAlH4
cleavage was 69%.
Resin 19. IR (KBr): 937, 1166, 1364 cmÀ1. Elemental analysis indicat-
ing 2.0% S, gives 79% yield. The yield determinated by LiAlH4 cleavage
was 80%.
ACKNOWLEDGMENT
This work was supported by the State Committee for Research Grant
No. T 09/PBZ.6.04
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Received in the Netherlands November 28, 2000

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