Formic Acid → 1-{[(Benzyloxy)(formyl)amino]methyl}cyclohexane-1-carboxylic acid

HRID 2055175Notes

Reaction equation

HRID 2055175 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:27]([OH:29])=[O:28])[CH2:26][CH2:25][CH2:24][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:27]([OH:29])=[O:28])[CH2:26][CH2:25][CH2:24][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 714169831-{[(Benzyloxy)amino]methyl}cyclohexane-1-carboxylic acid

Product 1

HCID 580161181-{[(Benzyloxy)(formyl)amino]methyl}cyclohexane-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cold solution of formic acid (15.3 mL, 0.4 mol) in dichloromethane (100 mL) at 0° C. under a nitrogen atmosphere was added acetic anhydride (5.75 mL, 60 mmol). After 1 h, a solution of 1-(benzyloxyamino-methyl)-cyclohexanecarboxylic acid from Preparation 19 (4.41 mmol theoretical) in dichloromethane (50 mL) was added. The mixture was stirred at room temperature for 18 h and was concentrated in vacuo. Brine (100 mL) was added and the mixture was extracted with dichloromethane (100 mL×2). The combined organic extracts were dried (MgSO4) and were evaporated in vacuo to yield the title compound as a pale, orange oil (1.77 g, 100%). MH+292.

Workup

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

Sources & evidence

ORD record
ord-1fa3d1f442664c35a64d7a4cba9c3d6f
Source dataset
uspto-grants-2008_02
Patent number
US07332485B2

Reaction notes

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