Sodium borohydride → HCID 57678374, compound

HRID 491876Notes

Reaction equation

HRID 491876 reaction equation
C[O:2][C:3](=O)[CH:4]([NH:11][C:12](=[O:40])[CH2:13][CH2:14][CH:15]([N:22]1[CH2:31][C:30]2[C:25](=[CH:26][CH:27]=[C:28]([O:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH:29]=2)[N:24]=[C:23]1[NH2:39])[CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[CH2:5][O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[BH4-].[Na+]>CO>[NH2:39][C:23]1[N:22]([C@H:15]([CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)[CH2:14][CH2:13][C:12]([NH:11][C@H:4]([CH2:5][O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH2:3][OH:2])=[O:40])[CH2:31][C:30]2[C:25](=[CH:26][CH:27]=[C:28]([O:32][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH:29]=2)[N:24]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydride3×HCID 67023460HCID 67023460, compound

Product 1

HCID 57678374HCID 57678374, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-[4-(2-amino-6-phenoxy-4H-quinazolin-3-yl)-4-cyclohexyl-butyrylamino]-3-tert-butoxy-propionic acid methyl ester (TFA salt, 50 mg) in methanol (5 mL), NaBH4 (0.04 g) was added slowly over a 30 minute period. The resulting solution was then stirred at room temperature overnight. LC/MS indicated very little product formed and most of the starting material remained. Additional NaBH4 (0.04 g) was added at room temperature, and the solution was stirred for an additional 8 hrs. Additional NaBH4 (0.08 g) was added over a 4 day period. LC/MS then indicated that most of the starting material was converted. The crude reaction mixture was purified by Gilson HPLC to yield the title compound as a white solid.

Workup

  1. customformed and most of the starting material
  2. stirringthe solution was stirred for an additional 8 hrs
  3. customThe crude reaction mixture
  4. customwas purified by Gilson HPLC

Sources & evidence

ORD record
ord-af1eaf6cb1e74d9a8162657e0d34daef
Source dataset
uspto-grants-2009_05
Patent number
US07531545B2

Reaction notes

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