Benzyl Alcohol → Benzyl 1-{{{[2(R)-Hydroxycyclopent-1(R)-yl]oxy}carbonyl}aminomethyl}-1-Cyclohexane Acetate

HRID 1795204Notes

Reaction equation

HRID 1795204 reaction equation
[OH:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[O:7][C:8]([NH:10][CH2:11][C:12]1([CH2:18][C:19]([OH:21])=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:9].C1(N=C=NC2CCCCC2)CCCCC1.[CH2:37](O)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>CN(C1C=CN=CC=1)C.ClCCl>[OH:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[O:7][C:8]([NH:10][CH2:11][C:12]1([CH2:18][C:19]([O:21][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:9]

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 10868DicyclohexylcarbodiimideHCID 865905641-{{{[2(R)-Hydroxycyclopent-1(R)-yl]oxy}carbonyl}aminomethyl}-1-Cyclohexane Acetic Acid

Product 1

HCID 86590565Benzyl 1-{{{[2(R)-Hydroxycyclopent-1(R)-yl]oxy}carbonyl}aminomethyl}-1-Cyclohexane AcetateYield 78.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of compound (49) (0.5 g, 1.67 mmol), 1,3-dicyclohexylcarbodiimide (1.0 g, 5.0 mmol) and DMAP (19 mg, 0.16 mmol) in dichloromethane (100 mL) at room temperature under nitrogen atmosphere was added benzyl alcohol (1.1 mL, 10 mmol). The reaction mixture was stirred at room temperature for 15 h (monitored by tlc and LC/MS), then filtered, and the white solid was washed with dichloromethane (2×15 mL). The combined filtrates were washed with water (2×25 mL), dried over Na2SO4 and concentrated in vacuo. The crude product was purified using flash chromatography on silica gel using hexane/ethyl acetate (2:1) as eluant to provide 0.51 g (78%) of compound (50) as a colorless liquid. 1H NMR (400 MHz, CDCl3): δ1.36–1.75 (14H, m); 1.99–2.10 (2H, m); 2.35 (2H, s); 3.17 (2H, d, J=6.8 Hz); 4.05 (1H, m); 4.65 (1H, m); 5.12 (2H, s); 5.34 (1H, t, J=6.8 Hz); 7.36 (5H, m). MS (ESI): m/z=390.22 (M+H+).

Workup

  1. filtrationfiltered
  2. washthe white solid was washed with dichloromethane (2×15 mL)
  3. washThe combined filtrates were washed with water (2×25 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified

Sources & evidence

ORD record
ord-393f63016bf14db39e04c7918dd66553
Source dataset
uspto-grants-2006_04
Patent number
US07026351B2

Reaction notes

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