Tetrahydrofuran → (S)-N-Carbobenzyloxy-3-(3,4-diformyloxyphenyl)-2-methylalanine

HRID 971591

Reaction equation

HRID 971591 reaction equation
[C:1]([NH:11][C@:12]([CH3:25])([C:22]([OH:24])=[O:23])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([OH:21])[CH:15]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH:26](OC(=O)C)=[O:27].[O:32]1CCC[CH2:33]1>>[C:1]([NH:11][C@:12]([CH3:25])([C:22]([OH:24])=[O:23])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH:26]=[O:27])=[C:16]([O:21][CH:33]=[O:32])[CH:15]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 75269Acetic-formic anhydrideHCID 18595367(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid

Product 1

HCID 54440584(S)-N-Carbobenzyloxy-3-(3,4-diformyloxyphenyl)-2-methylalanineYield 100%

Procedure

A solution of (S)-N-carbobenzyloxy-3-(3,4-dihydroxyphenyl)-2-methylalanine (0.35 g, 1 mmol) and acetic formic anhydride (0.36 g, 4 mmol) in anhydrous tetrahydrofuran (5 ml) is stirred 24 hours at 20°-25° under dry N2. The solvent is evaporated in vacuo and the residue is dried further at 0.1mm/25° for 2 hours. The product (A) (0.4g, 100%) is obtained as an oil.

Workup

  1. customThe solvent is evaporated in vacuo
  2. customthe residue is dried further at 0.1mm/25° for 2 hours

Sources & evidence

ORD record
ord-3f0910666326437e8a5216fc9950aee0
Source dataset
uspto-grants-1979_07
Patent number
US04160712

Linked notes

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