Formic Acid → 1-[(Benzyloxy-formyl-amino)-methyl]-4,4-dimethyl-cyclohexanecarboxylic acid

HRID 2055185Notes

Reaction equation

HRID 2055185 reaction equation
[CH:1](O)=[O:2].C(OC(=O)C)(=O)C.[CH2:11]([O:18][NH:19][CH2:20][C:21]1([C:29]([OH:31])=[O:30])[CH2:26][CH2:25][C:24]([CH3:28])([CH3:27])[CH2:23][CH2:22]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>ClCCl>[CH2:11]([O:18][N:19]([CH2:20][C:21]1([C:29]([OH:31])=[O:30])[CH2:26][CH2:25][C:24]([CH3:28])([CH3:27])[CH2:23][CH2:22]1)[CH:1]=[O:2])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 866064761-(Benzyloxyamino-methyl)-4,4-dimethyl-cyclohexanecarboxylic acid

Product 1

HCID 866064771-[(Benzyloxy-formyl-amino)-methyl]-4,4-dimethyl-cyclohexanecarboxylic acidYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cold solution of formic acid (12.8 mL, 0.33 mol) in dichloromethane (50 mL) at 0° C. under a nitrogen atmosphere was added acetic anhydride (4.8 mL, 51 mmol). After 1 h, a solution of 1-(benzyloxyamino-methyl)-4,4-dimethyl-cyclohexanecarboxylic acid from Preparation 30 (5.11 mmol theoretical) in dichloromethane (50 mL) was added. The reaction was stirred at room temperature for 18 h and was concentrated in vacuo. Water (100 mL) was added and the mixture was extracted with dichloromethane (50 mL×5). The combined organic extracts were dried (MgSO4) and were evaporated in vacuo to yield the title compound (1.55 g, 95%). MH+320.

Workup

  1. additionwas added
  2. concentrationwas concentrated in vacuo
  3. additionWater (100 mL) was added
  4. extractionthe mixture was extracted with dichloromethane (50 mL×5)
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. customwere evaporated in vacuo

Sources & evidence

ORD record
ord-8e21bd3504164448a5244c7966214512
Source dataset
uspto-grants-2008_02
Patent number
US07332485B2

Reaction notes

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