1'-acetyl-6-(acetyloxy)-6'-bromo-1',2',8,8a,9,10-hexahydro-6-methyl-2'-oxo-2,4-bis(phenylmethoxy)spiropyrimido<4,5-b><1,4>diazepine-7(6H),3'-<3H>indole>-8-carboxylic acid

Base Information

• Chemical Name: 1'-acetyl-6-(acetyloxy)-6'-bromo-1',2',8,8a,9,10-hexahydro-6-methyl-2'-oxo-2,4-bis(phenylmethoxy)spiropyrimido<4,5-b><1,4>diazepine-7(6H),3'-<3H>indole>-8-carboxylic acid
• CAS No.: 109714-11-6
• Molecular Formula: C₃₇H₃₂BrN₅O₈
• Molecular Weight: 754.594

Synonyms:1'-acetyl-6-(acetyloxy)-6'-bromo-1',2',8,8a,9,10-hexahydro-6-methyl-2'-oxo-2,4-bis(phenylmethoxy)spiropyrimido<4,5-b><1,4>diazepine-7(6H),3'-<3H>indole>-8-carboxylic acid

Chemical Property of 1'-acetyl-6-(acetyloxy)-6'-bromo-1',2',8,8a,9,10-hexahydro-6-methyl-2'-oxo-2,4-bis(phenylmethoxy)spiropyrimido<4,5-b><1,4>diazepine-7(6H),3'-<3H>indole>-8-carboxylic acid

Chemical Property:

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Technology Process of 1'-acetyl-6-(acetyloxy)-6'-bromo-1',2',8,8a,9,10-hexahydro-6-methyl-2'-oxo-2,4-bis(phenylmethoxy)spiropyrimido<4,5-b><1,4>diazepine-7(6H),3'-<3H>indole>-8-carboxylic acid

There total 9 articles about 1'-acetyl-6-(acetyloxy)-6'-bromo-1',2',8,8a,9,10-hexahydro-6-methyl-2'-oxo-2,4-bis(phenylmethoxy)spiropyrimido<4,5-b><1,4>diazepine-7(6H),3'-<3H>indole>-8-carboxylic acid 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: 98.0%

2-(methylsulfonyl)ethyl 1'-acetyl-6-(acetyloxy)-6'-bromo-1',2',8,8a,9,10-hexahydro-6-methyl-2'-oxo-2,4-bis(phenylmethoxy)spiropyrimido<4,5-b><1,4>diazepine-7(6H),3'-<3H>indole>-8-carboxylate (109681-06-3) → 1'-acetyl-6-(acetyloxy)-6'-bromo-1',2',8,8a,9,10-hexahydro-6-methyl-2'-oxo-2,4-bis(phenylmethoxy)spiropyrimido<4,5-b><1,4>diazepine-7(6H),3'-<3H>indole>-8-carboxylic acid (109714-11-6)

Guidance literature:

With sodium hydrogencarbonate; sodium carbonate; In water; acetone; for 3h; Ambient temperature; pH 10.2;

DOI:10.1016/S0040-4020(01)86990-8

Reference yield:

2-(methylthio)ethyl 6-bromo-2,3-dihydro-α-<<<5-nitro-2,6-bis(phenylmethoxy)-4-pyrimidinyl>amino>acetyl>-2-oxo-1H-indole-3-acetate (94779-74-5) → 1'-acetyl-6-(acetyloxy)-6'-bromo-1',2',8,8a,9,10-hexahydro-6-methyl-2'-oxo-2,4-bis(phenylmethoxy)spiropyrimido<4,5-b><1,4>diazepine-7(6H),3'-<3H>indole>-8-carboxylic acid (109714-11-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 80 percent Turnov_. / tetrahydrofuran / 0.5 h / -60 °C

2: 91 percent / 80percent m-CPBA / CH₂Cl₂ / 0.33 h / 5 °C

3: 95 percent / pyridine / 0.17 h / -18 °C

4: 1.) OsO₄, 2.) NaHSO₃ / 1.) THF, ether, pyridine, 0 deg C, 2.) pyridine, H₂O, 1 h, room temp.

5: 73 percent / SOCl₂ / CH₂Cl₂; pyridine / 0.17 h / -15 °C

6: 1.) Zn, AcOH, 2.) CSA / 1.) MeOH, CH₂Cl₂, 10 min, room temp., 2.) CH₂Cl₂, room temp., 10 min

7: 72 percent / 4-dimethylaminopyridine / tetrahydrofuran / 1.5 h / 5 - 20 °C

8: 98 percent / NaHCO₃, Na₂CO₃ / acetone; H₂O / 3 h / Ambient temperature; pH 10.2

With pyridine; dmap; osmium(VIII) oxide; thionyl chloride; camphor-10-sulfonic acid; sodium hydrogencarbonate; sodium carbonate; sodium hydrogensulfite; acetic acid; 3-chloro-benzenecarboperoxoic acid; zinc; In tetrahydrofuran; pyridine; dichloromethane; water; acetone;

DOI:10.1016/S0040-4020(01)86990-8

Reference yield:

2-(methylsulfonyl)ethyl 6'-bromo-1',2'-dihydro-3,5-dihydroxy-5-methyl-3-<<<5-nitro-2,6-bis(phenylmethoxy)-4-pyrimidinyl>amino>methyl>-2',4-dioxospiroindole>-2-carboxylate (109681-04-1) → 1'-acetyl-6-(acetyloxy)-6'-bromo-1',2',8,8a,9,10-hexahydro-6-methyl-2'-oxo-2,4-bis(phenylmethoxy)spiropyrimido<4,5-b><1,4>diazepine-7(6H),3'-<3H>indole>-8-carboxylic acid (109714-11-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 73 percent / SOCl₂ / CH₂Cl₂; pyridine / 0.17 h / -15 °C

2: 1.) Zn, AcOH, 2.) CSA / 1.) MeOH, CH₂Cl₂, 10 min, room temp., 2.) CH₂Cl₂, room temp., 10 min

3: 72 percent / 4-dimethylaminopyridine / tetrahydrofuran / 1.5 h / 5 - 20 °C

4: 98 percent / NaHCO₃, Na₂CO₃ / acetone; H₂O / 3 h / Ambient temperature; pH 10.2

With dmap; thionyl chloride; camphor-10-sulfonic acid; sodium hydrogencarbonate; sodium carbonate; acetic acid; zinc; In tetrahydrofuran; pyridine; dichloromethane; water; acetone;

DOI:10.1016/S0040-4020(01)86990-8

upstream raw materials:

2-(methylsulfonyl)ethyl 1'-acetyl-6-(acetyloxy)-6'-bromo-1',2',8,8a,9,10-hexahydro-6-methyl-2'-oxo-2,4-bis(phenylmethoxy)spiropyrimido<4,5-b><1,4>diazepine-7(6H),3'-<3H>indole>-8-carboxylate

3-[(2,6-Bis-benzyloxy-5-nitro-pyrimidin-4-ylamino)-methyl]-2-(6-bromo-2-oxo-2,3-dihydro-1H-indol-3-yl)-3-hydroxy-hex-4-ynoic acid 2-methylsulfanyl-ethyl ester

2-(methylsulfonyl)ethyl 6-bromo-2,3-dihydro-α-<1-hydroxy-1-<<<5-nitro-2,6-bis(phenylmethoxy)-4-pyrimidinyl>amino>methyl>-2-butynyl>-2-oxo-1H-indole-3-acetate

2-(methylsulfonyl)ethyl 6'-bromo-1',2'-dihydro-3,5-dihydroxy-5-methyl-3-<<<5-nitro-2,6-bis(phenylmethoxy)-4-pyrimidinyl>amino>methyl>-2',4-dioxospiroindole>-2-carboxylate

Downstream raw materials:

C₅₄H₅₈BrN₅O₁₄

C₆₄H₇₂BrN₅O₂₂

C₅₄H₆₂BrN₅O₁₇

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