tert-Butyl bromoacetate → N-Benzyloxycarbonyl-3-[4-(tert-butoxycarbonylmethoxy)-phenyl]-alanine-tert-butyl ester

HRID 1459110Notes

Reaction equation

HRID 1459110 reaction equation
[C:1]([O:5][C:6](=[O:27])[C@H:7]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)[NH:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])([CH3:4])([CH3:3])[CH3:2].[C:28]([O:32][C:33](=[O:36])[CH2:34]Br)([CH3:31])([CH3:30])[CH3:29]>>[C:1]([O:5][C:6](=[O:27])[C@H:7]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([O:26][CH2:34][C:33]([O:32][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:36])=[CH:24][CH:25]=1)[NH:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 79177tert-Butyl bromoacetateHCID 11428694Z-Tyr-OtBu

Product 1

HCID 22940773N-Benzyloxycarbonyl-3-[4-(tert-butoxycarbonylmethoxy)-phenyl]-alanine-tert-butyl ester

Procedure

5.57 g (15 mmol) of N-benzyloxycarbonyl-tyrosine-tert-butyl ester is reacted with bromoacetic acid-tert-butyl ester to alkylated phenol analogously to Example 3a).

Sources & evidence

ORD record
ord-2af71e2039a648d1b44c0c32e17d84f1
Source dataset
uspto-grants-1998_12
Patent number
US05853699

Reaction notes

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