D-Phenylalanine, 4-chloro-N-[(1,1-dimethylethoxy)carbonyl]-, 2-bromoethyl ester

Base Information

Chemical Name:D-Phenylalanine, 4-chloro-N-[(1,1-dimethylethoxy)carbonyl]-, 2-bromoethyl ester
CAS No.:139377-30-3
Molecular Formula:C16H21BrClNO4
Molecular Weight:406.704
Hs Code.:

Synonyms:

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Chemical Property of D-Phenylalanine, 4-chloro-N-[(1,1-dimethylethoxy)carbonyl]-, 2-bromoethyl ester

Chemical Property:

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Technology Process of D-Phenylalanine, 4-chloro-N-[(1,1-dimethylethoxy)carbonyl]-, 2-bromoethyl ester

There total 8 articles about D-Phenylalanine, 4-chloro-N-[(1,1-dimethylethoxy)carbonyl]-, 2-bromoethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 57292-44-1
N-Boc-D-(4-Cl)Phe-OH

: 540-51-2
2-bromoethanol

: 139377-30-3
D-(-)-N-<(1,1-dimethylethoxy)carbonyl>-4-chlorophenylalanine 2-bromoethyl ester

Guidance literature:: With pyridine; dicyclohexyl-carbodiimide; Yield given. Multistep reaction; 1) acetonitrile, DMF, 0 deg C, 2) 0 deg C, 16 h;
DOI:10.1021/jo00032a028

Reference yield:

: 2019-34-3
3-(4-chlorophenyl)propanoic acid

: 139377-30-3
D-(-)-N-<(1,1-dimethylethoxy)carbonyl>-4-chlorophenylalanine 2-bromoethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: Et₃N / tetrahydrofuran / a) -78 deg C, 10 min, b) 0 deg C, 30 min

2: 1) n-BuLi / 1) hexane, THF, -78 deg C, 2) a) -78 deg C, 15 min, b) up to room temp., 45 min

3: 1) KHMDS, 2) trisyl azide / 1) THF, -78 deg C, 30 min, 2) THF, -78 deg C, 2 min

4: aq. LiOH, 30percent H₂O₂ / tetrahydrofuran; H₂O / 1 h / 0 °C

5: H₂ / 10percent Pd/C / ethyl acetate / 760 Torr / Ambient temperature

6: 1) pyridine, 2) DCC / 1) acetonitrile, DMF, 0 deg C, 2) 0 deg C, 16 h

With pyridine; lithium hydroxide; n-butyllithium; 2,4,6-Triisopropylbenzenesulfonyl azide; hydrogen; dihydrogen peroxide; potassium hexamethylsilazane; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; water; ethyl acetate;
DOI:10.1021/jo00032a028

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 139377-30-3
D-(-)-N-<(1,1-dimethylethoxy)carbonyl>-4-chlorophenylalanine 2-bromoethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: H₂ / 10percent Pd/C / ethyl acetate / 760 Torr / Ambient temperature

2: 1) pyridine, 2) DCC / 1) acetonitrile, DMF, 0 deg C, 2) 0 deg C, 16 h

With pyridine; hydrogen; dicyclohexyl-carbodiimide; palladium on activated charcoal; In ethyl acetate;
DOI:10.1021/jo00032a028