Methanol → HCID 178474737, compound

HRID 1613496Notes

Reaction equation

HRID 1613496 reaction equation
[C:1]([O:5][C:6](=[O:31])[CH:7]([CH2:26][CH2:27][CH2:28][CH2:29][NH2:30])[CH2:8][C:9]1([C:14](=[O:25])[NH:15][C@H:16]2[CH2:21][CH2:20][C@@H:19]([C:22]([OH:24])=[O:23])[CH2:18][CH2:17]2)[CH2:13][CH2:12][CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:39](OC(=O)C)(=[O:41])[CH3:40].CO>ClCCl>[C:1]([O:5][C:6](=[O:31])[CH:7]([CH2:26][CH2:27][CH2:28][CH2:29][NH:30][C:39](=[O:41])[CH3:40])[CH2:8][C:9]1([C:14](=[O:25])[NH:15][C@H:16]2[CH2:17][CH2:18][C@@H:19]([C:22]([OH:24])=[O:23])[CH2:20][CH2:21]2)[CH2:13][CH2:12][CH2:11][CH2:10]1)([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 178450994HCID 178450994, compound

Product 1

HCID 178474737HCID 178474737, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-(4-Aminobutyl)-3-{1-[(cis-4-carboxy-cyclohexyl)carbamoyl]cyclopentyl}propanoic acid t-butyl ester (280 mg, 0.64 mmole) was dissolved in dichloromethane (30 ml) and treated with triethylamine (152 mg, 1.51 mmole) and acetic anhydride (78 mg, 0.76 mmole). After 20 minutes at room temperature the solvent was evaporated and the residue was dissolved in ethyl acetate (50 ml), washed with 1N hydrochloric acid (50 ml) and water (2×50 ml). The organic layer was separated, dried over magnesium sulphate and evaporated to give a colourless foam. Chromatography on silica gel eluting with a mixture of methanol and dichloromethane (1:19-1:4 by volume) and evaporation of the appropriate fractions gave the title product as a colourless foam (273 mg, 89%). Found: C,60.09; H,8.68; N,4.99. C26H44N2O5,0.6 CH2Cl2 requires, C,60.10; H,8.57; N,5.27%.

Workup

  1. customAfter 20 minutes at room temperature the solvent was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate (50 ml)
  3. washwashed with 1N hydrochloric acid (50 ml) and water (2×50 ml)
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customto give a colourless foam

Sources & evidence

ORD record
ord-84e0863f46104ff9a22f91ab44c3ba95
Source dataset
uspto-grants-1993_03
Patent number
US05192800

Reaction notes

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