Water → HCID 86752526, compound

HRID 1289248Notes

Reaction equation

HRID 1289248 reaction equation
[CH2:1]([C@@:8]([C:38]([OH:40])=[O:39])([CH2:17][CH2:18][C:19]([NH:21][CH:22]([C:27]1[CH:32]=[CH:31][C:30]([CH2:33][C:34]([O:36][CH3:37])=[O:35])=[CH:29][CH:28]=1)[C:23]([O:25][CH3:26])=[O:24])=[O:20])[NH:9]C(OC(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.O>ClCCl>[CH2:1]([C@@:8]([C:38]([OH:40])=[O:39])([CH2:17][CH2:18][C:19]([NH:21][CH:22]([C:27]1[CH:28]=[CH:29][C:30]([CH2:33][C:34]([O:36][CH3:37])=[O:35])=[CH:31][CH:32]=1)[C:23]([O:25][CH3:26])=[O:24])=[O:20])[NH2:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 86752527HCID 86752527, compound

Product 1

HCID 86752526HCID 86752526, compoundYield 127.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl (2RS)-2-{N-[α-benzyl-N-(tert-butoxycarbonyl)-L-γ-glutamyl]amino}-2-[p-(methoxycarbonylmethyl)phenyl]acetate (1.35 g, 2.4 mmol) in 5 ml of dichloromethane was added 5 ml of TFA and 0.5 ml of water. After stirring for 1 hour at room temperature the solution was evaporated to dryness and the resulting solid was azeotroped with toluene to give methyl (2RS)-2-[N-(α-benzyl-L-γ-glutamyl)-amino]-2-[p-(methoxycarbonylmethyl)phenyl]acetate (1.4 g) as a gummy solid;

Workup

  1. customwas evaporated to dryness
  2. customthe resulting solid was azeotroped with toluene

Sources & evidence

ORD record
ord-fbc7c416575a4463a9bd215473cdc14e
Source dataset
uspto-grants-1998_05
Patent number
US05747499

Reaction notes

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