Acetic Anhydride → (+/-)-Acetic acid (1SR,3RS,4RS)-3-{[1-(3,4-biscyclopropylmethoxyphenyl)methanoyl]amino}-4-(3,4-dimethoxyphenyl)cyclohexyl ester

HRID 220099Notes

Reaction equation

HRID 220099 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:29]=[CH:30][C:31]=2[O:32][CH2:33][CH:34]2[CH2:36][CH2:35]2)[C:9]([NH:11][CH:12]2[CH2:17][CH:16]([OH:18])[CH2:15][CH2:14][CH:13]2[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=2)=[O:10])[CH2:3][CH2:2]1.[C:37](OC(=O)C)(=[O:39])[CH3:38]>>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([C:9]([NH:11][CH:12]3[CH:13]([C:19]4[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=4)[CH2:14][CH2:15][CH:16]([O:18][C:37](=[O:39])[CH3:38])[CH2:17]3)=[O:10])[CH:29]=[CH:30][C:31]=2[O:32][CH2:33][CH:34]2[CH2:35][CH2:36]2)[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 68986614(+/-)-3,4-bis-cyclopropylmethoxy-N-[(1RS,2RS,5RS)-2-(3,4-dimethoxyphenyl)-5-hydroxycyclohexyl]benzamide2×

Product 1

HCID 86601278(+/-)-Acetic acid (1SR,3RS,4RS)-3-{[1-(3,4-biscyclopropylmethoxyphenyl)methanoyl]amino}-4-(3,4-dimethoxyphenyl)cyclohexyl ester

Conditions

Temperature
100 °C

Procedure

3.2 g of (±)-3,4-bis-cyclopropylmethoxy-N-[(1RS,2RS,5RS)-2-(3,4-dimethoxyphenyl)-5-hydroxycyclohexyl]benzamide (compound D1) are dissolved in 70 ml of acetic anhydride and the solution is heated to 100° C. for 5 h. The solution is concentrated and the residue is recrystallized in ethanol. 3.15 g of the title compound of m.p. 148-151° C. are obtained.

Workup

  1. concentrationThe solution is concentrated
  2. customthe residue is recrystallized in ethanol

Sources & evidence

ORD record
ord-e2663948d83942a6a60097920feb5397
Source dataset
uspto-grants-2012_06
Patent number
US08202880B2

Reaction notes

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