Formic Acid → HCID 18342538, compound

HRID 2301184Notes

Reaction equation

HRID 2301184 reaction equation
COC1C=CC(CO[C:9](=O)[C@H:10]([N:17]2[CH2:21][C@H:20](C3C=CC=CC=3)[C@@H:19]([CH2:28][N:29]3[CH2:34][CH2:33][CH:32]([CH2:35][O:36][CH2:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[CH2:31][CH2:30]3)[CH2:18]2)[CH:11]2[CH2:16][CH2:15][CH2:14]C[CH2:12]2)=CC=1.[CH:47]([OH:49])=[O:48]>>[CH2:37]([O:36][CH2:35][CH:32]1[CH2:33][CH2:34][N:29]([CH2:28][C@@H:19]2[C@@H:20]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH2:21][N:17]([C@@H:10]3[CH2:9][CH2:14][CH2:15][CH2:16][CH:11]3[CH2:12][C:47]([OH:49])=[O:48])[CH2:18]2)[CH2:30][CH2:31]1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 53913449HCID 53913449, compound

Product 1

HCID 18342538HCID 18342538, compound

Procedure

A solution of α-(R)-(3-(S)-((4-(benzyloxymethyl)piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid para-methoxybenzyl ester (30 mg, 0.048 mmol) 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 a second portion 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 19 mg of the title compound as a colorless brittle glass. 1H NMR (400 MHz, CD3OD): δ 7.39-7.22 (m, 10H), 4.45 (s, 2H), 3.59 (dd, J=11, 8 Hz, 2H), 3.48 (d, J=4 Hz, 1H), 3.46-3.35 (m, 1H), 3.28 (d, J=6 Hz, 2H), 3.12 (td, J=10, 8 Hz, 1H), 2.93 (bd, J=11 Hz, 1H), 2.81-2.71 (m, 2H), 2.49 (dd, J=12, 10 Hz, 1H), 2.33 (dd, J=12, 3 Hz, 1H), 2.03 (bt, J=11 Hz, 1H), 1.92-1.12 (m, 18H); ESI−MS 505 (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-0e8488c98f914ea3a00e5cf881b0f33a
Source dataset
uspto-grants-2002_12
Patent number
US06498161B1

Reaction notes

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