HCID 70177531, compound → HCID 21341081, compound

HRID 2185563Notes

Reaction equation

HRID 2185563 reaction equation
[O:1]=[C:2]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][C@@H:12]2[C@@H:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:15][N:14]([C@H:23]([CH:36]3[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]3)[C:24]([O:26]CC3C=CC(OC)=CC=3)=[O:25])[CH2:13]2)[CH2:7][CH2:6]1>C(O)=O>[O:1]=[C:2]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][C@@H:12]2[C@@H:16]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:15][N:14]([C@H:23]([CH:36]3[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]3)[C:24]([OH:26])=[O:25])[CH2:13]2)[CH2:7][CH2:6]1

Participants

3

Reactant 1

HCID 70177531HCID 70177531, compound

Product 1

HCID 21341081HCID 21341081, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 2-(R)-(3-(S)-(4-(3-oxo-3-phenylpropyl)piperidin-1-yl)methyl-4-(S)-phenylpyrrolidin-1-yl)-2-(cyclohexyl)acetic acid 4-(methoxy)benzyl ester (29 mg, 0.046 mmol, from Step E) in 96% formic acid (2.0 mL) was stirred at rt. After 2 h, the formic acid was evaporated at reduced pressure. Toluene was added and evaporated, and this was repeated with two additional portions of toluene. The crude product was purified by flash column chromatography on silica gel packed in CH2Cl2. Elution with 5% CH3OH/1% conc. aq. NH4OH/CH2Cl2 followed by 10% CH3OH/2% conc. aq. NH4OH/CH2Cl2 gave 17 mg of the title compound as a colorless glass. ESI-MS: 517 (M+H).

Workup

  1. customthe formic acid was evaporated at reduced pressure
  2. additionToluene was added
  3. customevaporated
  4. customThe crude product was purified by flash column chromatography on silica gel
  5. washElution with 5% CH3OH/1% conc. aq. NH4OH/CH2Cl2

Sources & evidence

ORD record
ord-dff249fd893e4bb186345f18cc00cf9f
Source dataset
uspto-grants-2002_06
Patent number
US06399619B1

Reaction notes

Loading…