HCID 86619280, compound → HCID 68606742, compound

HRID 2267675Notes

Reaction equation

HRID 2267675 reaction equation
[CH:1]1([CH2:4][N:5]([C@@H:17]2[CH2:22][CH2:21][CH2:20][CH2:19][C@H:18]2[OH:23])[C:6]([C@H:8]2[C@H:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:9]2)=[O:7])[CH2:3][CH2:2]1>C(#N)C.C(O)(C(F)(F)F)=O>[CH:1]1([CH2:4][N:5]2[C@@H:17]3[CH2:22][CH2:21][CH2:20][CH2:19][C@H:18]3[O:23][C@@H:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C@@H:8]([OH:9])[C:6]2=[O:7])[CH2:2][CH2:3]1

Participants

3

Reactant 1

HCID 86619280HCID 86619280, compound

Product 1

HCID 68606742HCID 68606742, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 21924481TFA acetonitrileSolvent

Procedure

A solution of (2R,3S)—N-(cyclopropylmethyl)-N-[(1R,2R)-2-hydroxycyclohexyl]-3-phenyloxirane-2-carboxamide (117b) (1.05 g, 3.33 mmol) in 125 mL acetonitrile/TFA (0.4%) was stirred for 6 hours. After evaporation the crude oil was purified by chromatography (CHCl3) to afford the title compound (850 mg, 81%). HPLC: 4.54 min (Method B). 1H NMR (300 MHz, CDCl3) δ0.37-0.44 (m, 2H), 0.49-0.57 (m, 2H), 0.85 (m, 1H), 1.03 (m, 1H), 1.14-1.50 (m, 2H), 1.66-1.80 (m, 2H), 1.83-2.02 (m, 1H), 2.03-2.16 (m, 2H), 3.32 (dd, 1H, J=7 Hz, J=14 Hz), 3.60 (in 1H), 3.74 (m, 1H), 3.85 (dd, 1H, J=7 Hz, J=14 Hz), 4.34 (m, 1H), 4.60 (m, 1H), 7.27-7.40 (m, 5H).

Workup

  1. customAfter evaporation the crude oil
  2. customwas purified by chromatography (CHCl3)

Sources & evidence

ORD record
ord-b0e95a18c05f4ae3b6ad9a17070a1146
Source dataset
uspto-grants-2010_12
Patent number
US07858776B2

Reaction notes

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