Water → HCID 3011828, compound

HRID 850860Notes

Reaction equation

HRID 850860 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][C@H:66]([CH:69](OC)[O:70]C)[CH2:67][CH3:68])=[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.FC(F)(F)C(O)=O.O>ClCCl.C1(C)C=CC=CC=1>[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][C@@H:66]([CH2:67][CH3:68])[CH:69]=[O:70])=[O:64])[CH2:59][CH:60]([CH3:62])[CH3:61])=[O:56])[C:51]([CH3:52])([CH3:53])[CH3:54])=[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

6

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 86753707HCID 86753707, compound

Product 1

HCID 3011828HCID 3011828, compoundYield 30.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

0.1 g (0.1 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(S)-(dimethoxymethyl)propyl]-L-leucinamide was dissolved in 3 ml of dichloromethane, 3 ml of trifluoroacetic acid and 90 mg of water and the mixture was stirred at room temperature for 30 minutes. The solution was diluted with 20 ml of toluene and the solvent was removed by evaporation. The resulting white solid was triturated with diethyl ether and filtered off. The solid was purified by RP-HPLC on a C18 Dynamax column (pore size 300 Å; column size 21.4 mm×50 mm). The elution gradient comprised 90% SSA 10% SSB to 95% SSB 5% SSA over 8.5 minutes. After lyophilization overnight there were obtained 25 mg of 2(S)-[[N-[N-[N-[N-[N-(3-carboxypropionyl)-L-α-aspartyl]-L-α-glutamyl]-2-methyl-L-phenylalanyl]-3-methyl-L-valyl]-L-leucyl]amino]butyraldehyde as a white foam. MS: m/e 819.5 [M+H]+.

Workup

  1. customthe solvent was removed by evaporation
  2. customThe resulting white solid was triturated with diethyl ether
  3. filtrationfiltered off
  4. customThe solid was purified by RP-HPLC on a C18 Dynamax column (pore size 300 Å; column size 21.4 mm×50 mm)
  5. customSSA over 8.5 minutes

Sources & evidence

ORD record
ord-a02158ea772749f6af685badd4b768a2
Source dataset
uspto-grants-2000_01
Patent number
US06018020

Reaction notes

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