Water → HCID 178513888, compound

HRID 1613487Notes

Reaction equation

HRID 1613487 reaction equation
[CH2:1]([O:8][C:9](=[O:52])[CH:10]([CH2:36][CH2:37][C:38](=[O:51])[NH:39]CC1C=CC(OC)=CC=1OC)[CH2:11][C:12]1([C:17](=[O:35])[NH:18][C@H:19]2[CH2:24][CH2:23][C@@H:22]([C:25]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:26])[CH2:21][CH2:20]2)[CH2:16][CH2:15][CH2:14][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C(=O)([O-])O.[Na+]>FC(F)(F)C(O)=O>[CH2:1]([O:8][C:9](=[O:52])[CH:10]([CH2:36][CH2:37][C:38](=[O:51])[NH2:39])[CH2:11][C:12]1([C:17](=[O:35])[NH:18][C@H:19]2[CH2:20][CH2:21][C@@H:22]([C:25]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:26])[CH2:23][CH2:24]2)[CH2:13][CH2:14][CH2:15][CH2:16]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 178491189HCID 178491189, compound

Product 1

HCID 178513888HCID 178513888, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

3-{1-[(cis-4-Benzyloxycarbonyl-cyclohexyl)carbamoyl]-cyclopentyl}-2-{2-[(2,4-dimethoxyphenyl)methylcarbamoyl]ethyl}propanoic acid benzyl ester (Example 164) (0.37 g, 0.52 mmole) was dissolved in trifluoroacetic acid (10 ml). After stirring for 18 hours at room temperature the deep pink reaction mixture was poured into iced water which was basified with sodium hydrogen carbonate and extracted with dichloromethane. The combined extracts were dried (Na2SO4) and evaporated under vacuum. The residue was purified by column chromatography on silica gel eluting with dichloromethane-diethyl ether and methanoldichloromethane mixtures to yield the title ester (110 mg, 38%). Rf 0.25 (silica; ethylacetate).

Workup

  1. customthe deep pink reaction mixture
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. customevaporated under vacuum
  5. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane-diethyl ether and methanoldichloromethane mixtures

Sources & evidence

ORD record
ord-bd2e7557851a428bb524dab9601809b9
Source dataset
uspto-grants-1993_03
Patent number
US05192800

Reaction notes

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