Ethylmorpholine → HCID 54201682, compound

HRID 850897Notes

Reaction equation

HRID 850897 reaction equation
C(N1CC[O:6][CH2:5][CH2:4]1)C.C(OC(=O)C)(=O)C.[CH2:16]([O:23][C:24](=[O:68])[C@H:25]([CH2:64][CH:65]([CH3:67])[CH3:66])[NH:26][C:27](=[O:63])[C@H:28]([C:59]([CH3:62])([CH3:61])[CH3:60])[NH:29][C:30](=[O:58])[C@H:31]([CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=1[CH3:57])[NH:32][C:33](=[O:49])[C@@H:34]([CH:46]([CH3:48])[CH3:47])[NH:35][C:36](=[O:45])[C@H:37]([CH2:39][O:40][C:41]([CH3:44])([CH3:43])[CH3:42])[NH2:38])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>ClCCl>[CH2:16]([O:23][C:24](=[O:68])[C@H:25]([CH2:64][CH:65]([CH3:67])[CH3:66])[NH:26][C:27](=[O:63])[C@H:28]([C:59]([CH3:62])([CH3:61])[CH3:60])[NH:29][C:30](=[O:58])[C@H:31]([CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=1[CH3:57])[NH:32][C:33](=[O:49])[C@@H:34]([CH:46]([CH3:47])[CH3:48])[NH:35][C:36](=[O:45])[C@H:37]([CH2:39][O:40][C:41]([CH3:42])([CH3:44])[CH3:43])[NH:38][C:5](=[O:6])[CH3:4])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 7525EthylmorpholineHCID 7918Acetic AnhydrideHCID 54062324HCID 54062324, compound

Product 1

HCID 54201682HCID 54201682, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.5 ml of N-ethylmorpholine and 0.37 ml of acetic anhydride were added in sequence to a solution of 1.95 g of N-[N-[N-[N-(O-tert-butyl-L-seryl)-D-valyl]-2-methyl-L-phenylalanyl]-3-methyl-L-valyl]-L-leucine benzyl ester in 70 ml of anhydrous dichloromethane. The mixture was stirred at room temperature for 1 hour and was then washed in sequence with 5% aqueous citric acid solution, saturated aqueous sodium bicarbonate solution and saturated brine. The organic phase was dried over anhydrous magnesium sulphate and evaporated. Chromatography of the residue on silica using 5% methanol in dichloromethane for the elution gave afforded 1.45 g of N-[N-[N-[N-(N-acetyl-O-tert-butyl-L-seryl)-D-valyl]-2-methyl-L-phenylalanyl]-3-methyl-L-valyl]-L-leucine benzyl ester; MS: m/e 780.6 [M+H]+.

Workup

  1. washwas then washed in sequence with 5% aqueous citric acid solution, saturated aqueous sodium bicarbonate solution and saturated brine
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulphate
  3. customevaporated
  4. washChromatography of the residue on silica using 5% methanol in dichloromethane for the elution
  5. customgave

Sources & evidence

ORD record
ord-329ddc7e71454b478dbc83d4b1b08bbc
Source dataset
uspto-grants-2000_01
Patent number
US06018020

Reaction notes

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