tert-butyl N-[(2S)-4-methyl-1-oxopentan-2-yl]carbamate → (2S)-[2-[(t-Butoxycarbonyl)amino]-1-hydroxy-4-methylpentyl]bis(4-chlorophenyl)phosphine oxide

HRID 1683665Notes

Reaction equation

HRID 1683665 reaction equation
[NH:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:2]([CH:7]=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([PH:23](=[O:31])[C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)=[CH:19][CH:18]=1>>[C:12]([O:11][C:9]([NH:1][C@@H:2]([CH2:3][CH:4]([CH3:6])[CH3:5])[CH:7]([P:23](=[O:31])([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)[C:20]1[CH:21]=[CH:22][C:17]([Cl:16])=[CH:18][CH:19]=1)[OH:8])=[O:10])([CH3:13])([CH3:15])[CH3:14]

Participants

3

Reactant 2

HCID 104275tert-butyl N-[(2S)-4-methyl-1-oxopentan-2-yl]carbamateHCID 1785270301-chloro-4-(4-chlorophenyl)phosphonoylbenzene

Product 1

HCID 22873484(2S)-[2-[(t-Butoxycarbonyl)amino]-1-hydroxy-4-methylpentyl]bis(4-chlorophenyl)phosphine oxideYield 83%

Procedure

t-Boc-Leu-H; bis(4-chlorophenyl)phosphine oxide; 2.5 hours; yield 83% (2S)-[2-[(t-Butoxycarbonyl)amino]-1-hydroxy-4-methylpentyl]bis(4-chlorophenyl)phosphine oxide; MS: 486, 488 m/z (M+H)+, dichloro isotope pattern.

Workup

  1. custom2.5 hours

Sources & evidence

ORD record
ord-6868fdf58da1413eba4695a664ca8798
Source dataset
uspto-grants-1997_06
Patent number
US05639732

Reaction notes

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