HCID 86753716, compound → HCID 86753715, compound

HRID 850895Notes

Reaction equation

HRID 850895 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:71](OC)[O:72]C)[CH2:67]/[CH:68]=[CH:69]\[CH3:70])=[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>[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]/[CH:68]=[CH:69]\[CH3:70])[CH:71]=[O:72])=[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

5

Reactant 1

HCID 86753716HCID 86753716, compound

Product 1

HCID 86753715HCID 86753715, compoundYield 88.8%

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

0.05 g (0.04 mmol) of (Z)-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]-N 1-[1(S)-(dimethoxymethyl)-3-pentenyl]-L-leucinamide was dissolved in 4 ml of a 1:1 solution of dichloromethane and trifluoroacetic acid and containing 3 drops of water. The solution was stirred at room temperature for 1 hour. After removal of the solvent by evaporation the crude product was triturated using diethyl ether to afford 0.03 g of (Z)-2(S)-[[N-[N-[N-[N-[N-(3-carboxypropionyl)-L-alpha-aspartyl]-L-alpha-glutamyl]-2-methyl-L-phenylalanyl]-3-methyl-L-valyl]-L-leucyl]amino]-4-hexenal as a white solid; MS: m/e 845.7 [M+H]+.

Workup

  1. customAfter removal of the solvent
  2. customby evaporation the crude product
  3. customwas triturated

Sources & evidence

ORD record
ord-186b6315b64a4e02b00e4b7cb6d311e9
Source dataset
uspto-grants-2000_01
Patent number
US06018020

Reaction notes

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