Methanol → HCID 69629912, compound

HRID 1241469Notes

Reaction equation

HRID 1241469 reaction equation
[C:1]([O:5][C:6](=[O:45])[CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:17]2[CH:18]=[CH:19][C:20]([I:22])=[CH:21][C:16]=2[C:15](=[O:23])[N:14]([C@@H:24]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)[CH3:25])[C@@H:13]([C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][C:34]=2[O:40]CC=C)[C:12]1=[O:44])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].CO>C1COCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[C:1]([O:5][C:6](=[O:45])[CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:17]2[CH:18]=[CH:19][C:20]([I:22])=[CH:21][C:16]=2[C:15](=[O:23])[N:14]([C@@H:24]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)[CH3:25])[C@@H:13]([C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][C:34]=2[OH:40])[C:12]1=[O:44])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 69630694HCID 69630694, compound

Product 1

HCID 69629912HCID 69629912, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

5-[(3S)-3-(2-Allyloxy-4-chlorophenyl)-4-[(R)-1-(4-chlorophenyl)ethyl]-7-iodo-2,5-dioxo-1,4-benzodiazepin-1-yl]valeric acid tert-butyl ester (224 mg, 0.29 mmol) and dichloro bis(triphenylphosphine)palladium (II) (10 mg, 0.015 mmol) were dissolved at room temperature in THF (5 mL). Sodium borohydride (11 mg, 0.29 mmol) was added and the reaction was stirred under argon for 30 minutes. Methanol (10 mL) was added and the reaction was stirred for 15 additional minutes. The solvent was evaporated under vacuum and the residue was purified by column chromatography (AcOEt/Hexanes, 1:2) to give 200 mg of the title compound contaminated with 5-[(3S)-3-(2-Allyloxy-4-chlorophenyl)-4-[(R)-1-(4-chlorophenyl)ethyl]-2,5-dioxo-1,4-benzodiazepin-1-yl]valeric acid tert-butyl ester. This mixture was carried out to the next step without further purification.

Workup

  1. stirringthe reaction was stirred for 15 additional minutes
  2. customThe solvent was evaporated under vacuum
  3. customthe residue was purified by column chromatography (AcOEt/Hexanes, 1:2)

Sources & evidence

ORD record
ord-72a6cf9fce9a4ac599539a7feb3e1187
Source dataset
uspto-grants-2006_10
Patent number
US07115598B2

Reaction notes

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