Water → HCID 3011828, compound

HRID 362120Notes

Reaction equation

HRID 362120 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.ClCCl.FC(F)(F)C(O)=O.O>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 4

HCID 962WaterHCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 86753707HCID 86753707, compound

Product 1

HCID 3011828HCID 3011828, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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 in3 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 elutiongradient 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. waitThe elutiongradient comprised 90% SSA 10% SSB to 95% SSB 5% SSA over 8.5 minutes

Sources & evidence

ORD record
ord-2201d1f6d1ff4787944f7d4850d188fd
Source dataset
uspto-grants-1999_02
Patent number
US05866684

Reaction notes

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