HCID 86588818, compound → Tert-butyl (2R)-4-benzyl-2-hydroxymethyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carboxylate

HRID 1884532Notes

Reaction equation

HRID 1884532 reaction equation
F[C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:4][C:3]=1[CH2:15][N:16]([C:24](=[O:39])[C@@H:25]([CH2:37][OH:38])[NH:26]C(OCC1C=CC=CC=1)=O)[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.FC1C=CC(C(OC(C)(C)C)=O)=CC=1CN(C(=O)[C@@H](C)NC(OCC1C=CC=CC=1)=O)C>>[CH2:17]([N:16]1[CH2:15][C:3]2[CH:4]=[C:5]([C:6]([O:8][C:9]([CH3:11])([CH3:12])[CH3:10])=[O:7])[CH:13]=[CH:14][C:2]=2[NH:26][C@H:25]([CH2:37][OH:38])[C:24]1=[O:39])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 86588818HCID 86588818, compoundHCID 86588819tert-butyl (R)-4-fluoro-3-[[[N-(benzyloxycarbonyl)alaninyl]-methylamino]methyl]benzoate

Product 1

HCID 54251532Tert-butyl (2R)-4-benzyl-2-hydroxymethyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carboxylateYield 34%

Procedure

According to the procedure of Preparation 4 (d), except substituting tert-butyl (R)-4-fluoro-3-[[[N-(benzyloxycarbonyl)serinyl]benzylamino]methyl]benzoate (1.58 g, 3 mmole) for the tert-butyl (R)-4-fluoro-3-[[[N-(benzyloxycarbonyl)alaninyl]-methylamino]methyl]benzoate, the title compound (0.39 g, 34%) was prepared as an off-white solid following recrystallization from EtOAc/hexanes: MS (ES) m/e 383.0 (M+H)+.

Sources & evidence

ORD record
ord-9100c1b6f4a7466eb75b11e188f3a9a9
Source dataset
uspto-grants-2004_07
Patent number
US06765005B2

Reaction notes

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