Hydrochloric Acid → HCID 178447525, compound

HRID 1086728Notes

Reaction equation

HRID 1086728 reaction equation
[C:1](Cl)(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].[C:8]([O:12][C:13](=[O:45])[CH:14]([CH2:40][CH2:41][CH2:42][CH2:43][OH:44])[CH2:15][C:16]1([C:21](=[O:39])[NH:22][C@H:23]2[CH2:28][CH2:27][C@@H:26]([C:29]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[O:30])[CH2:25][CH2:24]2)[CH2:20][CH2:19][CH2:18][CH2:17]1)([CH3:11])([CH3:10])[CH3:9].Cl>N1C=CC=CC=1>[C:8]([O:12][C:13](=[O:45])[CH:14]([CH2:40][CH2:41][CH2:42][CH2:43][O:44][C:1](=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5])[CH2:15][C:16]1([C:21](=[O:39])[NH:22][C@H:23]2[CH2:28][CH2:27][C@@H:26]([C:29]([O:31][CH2:32][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)=[O:30])[CH2:25][CH2:24]2)[CH2:20][CH2:19][CH2:18][CH2:17]1)([CH3:10])([CH3:9])[CH3:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 61186Valeryl chlorideHCID 178450995HCID 178450995, compound

Product 1

HCID 178447525HCID 178447525, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Valeryl chloride (0.2 ml, 1.98 mmole) was added dropwise to a stirred, ice cold solution of 3-{1-[(cis-4-benzyloxycarbonylcyclohexyl)carbamoyl]cyclopentyl}-2-(4-hydroxybutyl)propanoic acid t-butyl ester (0.7 g, 1.32 mmole) in dry pyridine (5 ml). The mixture was allowed to stand overnight at room temperature and ice was added, the pH was adjusted to 3 by the addition of 2N hydrochloric acid and the mixture was extracted with diethyl ether. The organic extract was dried (Na2SO4) and evaporated to give a gum which was chromatographed on silica eluting with hexane containing increasing proportions of diethyl ether to give the title product as a gum (. . . g . . . %). Found: C,70.06; H,8.91; N,2.58. C36H55NO7 requires C,70.44; H,9.03; N,2.28%.

Workup

  1. additionice was added
  2. extractionthe mixture was extracted with diethyl ether
  3. extractionThe organic extract
  4. dry with materialwas dried (Na2SO4)
  5. customevaporated
  6. customto give a gum which
  7. customwas chromatographed on silica eluting with hexane containing
  8. temperatureincreasing proportions of diethyl ether

Sources & evidence

ORD record
ord-48822ccb835f4f02affc28e9000fe6ea
Source dataset
uspto-grants-1991_07
Patent number
US05030654

Reaction notes

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