Water → HCID 22942025, compound

HRID 362139Notes

Reaction equation

HRID 362139 reaction equation
C([O:5][C:6]([CH2:8][CH2:9][C:10]([NH:12][C@H:13]([C:22]([NH:24][C@H:25]([C:35]([NH:37][C@H:38]([C:47]([NH:49][C@H:50]([C:55]([NH:57][C@H:58]([C:63]([NH:65][CH:66]([CH:73](OC)[O:74]C)[CH2:67][C:68]1[CH:72]=[CH:71][S:70][CH:69]=1)=[O:64])[CH2:59][CH:60]([CH3:62])[CH3:61])=[O:56])[C:51]([CH3:54])([CH3:53])[CH3:52])=[O:48])[CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[CH3:46])=[O:36])[CH2:26][CH2:27][C:28](=[O:34])[O:29]C(C)(C)C)=[O:23])[CH2:14][C:15](=[O:21])[O:16]C(C)(C)C)=[O:11])=[O:7])(C)(C)C.O>ClCCl.FC(F)(F)C(O)=O>[C:6]([CH2:8][CH2:9][C:10]([NH:12][C@H:13]([C:22]([NH:24][C@H:25]([C:35]([NH:37][C@H:38]([C:47]([NH:49][C@H:50]([C:55]([NH:57][C@H:58]([C:63]([NH:65][CH:66]([CH2:67][C:68]1[CH:72]=[CH:71][S:70][CH:69]=1)[CH:73]=[O:74])=[O:64])[CH2:59][CH:60]([CH3:61])[CH3:62])=[O:56])[C:51]([CH3:54])([CH3:52])[CH3:53])=[O:48])[CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[CH3:46])=[O:36])[CH2:26][CH2:27][C:28](=[O:29])[OH:34])=[O:23])[CH2:14][C:15](=[O:16])[OH:21])=[O:11])([OH:7])=[O:5]

Participants

4

Reactant 2

HCID 962WaterHCID 22942090HCID 22942090, compound

Product 1

HCID 22942025HCID 22942025, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

0.065 g (0.06 mmol) of N2-[N-[N-[N-[N-[3-(tert-butoxycarbonyl)propionyl]-O-tert-butyl-L-α-aspartyl]-O-tert-butyl-L-α-glutamyl]-2-methyl-L-phenylalanyl]-3-methyl-L-valyl]-N1-[1(RS)-(dimethoxymethyl)-2-(3-thienyl)ethyl]-L-leucinamide wasdissolved in 10 ml of dichloromethane/trifluoroacetic acid (1:1) containing3 drops of water. The solution was stirred for 3 hours at room temperature.After removal of the solvent by evaporation the crude product was chromatographed on silica gel using dichloromethane:methanol:acetic acid:water (120:15:3:2) as the eluent to give 0.035 g of 2(RS)-[[N-[N-[N-[N-[N-(3-carboxypropionyl)-L-α-aspartyl-L-α-glutamyl]-2-methyl-L-phenylalanyl]-3-methyl-L-valyl]-L-leucyl]amino]-3(3-thienyl)propionaldehyde as a white solid; MS: m/e 887.7 [M+H]+.

Workup

  1. customAfter removal of the solvent
  2. customby evaporation the crude product
  3. customwas chromatographed on silica gel

Sources & evidence

ORD record
ord-c83b9bfa89364bcbae1b1d9204a17c99
Source dataset
uspto-grants-1999_02
Patent number
US05866684

Reaction notes

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