Water → HCID 70479570, compound

HRID 638092Notes

Reaction equation

HRID 638092 reaction equation
[CH3:1][C:2]([CH3:46])([O:4][C:5]([NH:7][C@@H:8]([CH2:42][CH:43]([CH3:45])[CH3:44])[C:9]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]([CH2:20][CH:21]2[NH:27][C:26](=[O:28])[C:25]3[CH:29]=[CH:30][CH:31]=[CH:32][C:24]=3[N:23]3[C:33](=[O:41])[C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][C:39]=4[N:40]=[C:22]23)[CH2:12]1)=[O:10])=[O:6])[CH3:3].C([BH3-])#N.[Na+].O>C(O)(=O)C>[OH2:4].[CH3:3][C:2]([CH3:46])([O:4][C:5]([NH:7][C@@H:8]([CH2:42][CH:43]([CH3:44])[CH3:45])[C:9]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]([CH2:20][CH:21]2[NH:27][C:26](=[O:28])[C:25]3[CH:29]=[CH:30][CH:31]=[CH:32][C:24]=3[N:23]3[C:33](=[O:41])[C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][C:39]=4[N:40]=[C:22]23)[CH2:12]1)=[O:10])=[O:6])[CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 54535366HCID 54535366, compound

Product 1

HCID 70479570HCID 70479570, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

7-[(1-[2(S)-((1,1-Dimethylethoxy)carbonyl)amino-4-methylpentanoyl]-2,3-dihydro-1H-indol-3-yl)-methyl]quinazolino(3,2-A)-1,4-benzodiazepin-5,13-(6H,7H)-dione (250 mg, 0.40 mmole) was dissolved in 4 ml of glacial acetic acid and treated at 10° with 101 mg (1.60 mmole) of sodium cyanoborohydride. After twenty minutes, the reaction mixture was poured into 50 ml of water and then extracted with ethyl acetate (4×40 ml). The combined organic extracts were washed with saturated sodium bicarbonate solution and brine, then dried (MgSO4) and concentrated. The crude product was purified by preparative thick layer chromatography on silica gel (97:3 chloroform-methanol elution) to give the analytical sample as a mixture of diastereomers.

Workup

  1. waitAfter twenty minutes
  2. extractionextracted with ethyl acetate (4×40 ml)
  3. washThe combined organic extracts were washed with saturated sodium bicarbonate solution and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by preparative thick layer chromatography on silica gel (97:3 chloroform-methanol elution)
  7. customto give the analytical sample
  8. additionas a mixture of diastereomers

Sources & evidence

ORD record
ord-be381e0125634c2d9044d590fae0502c
Source dataset
uspto-grants-1985_12
Patent number
US04559339

Reaction notes

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