Formic Acid → [1-Benzenesulfonyl-2-(3-benzyloxy-phenyl)-ethyl]-carbamic acid tert-butyl ester

HRID 1432332Notes

Reaction equation

HRID 1432332 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:15][CH:16]=O)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18](NC(=O)[O-])([CH3:21])([CH3:20])[CH3:19].[C:26]1([S:32]([O-:34])=[O:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[Na+].[CH:36]([OH:38])=[O:37].C(#[N:41])C>CCOC(C)=O>[C:18]([O:37][C:36](=[O:38])[NH:41][CH:16]([S:32]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:34])=[O:33])[CH2:15][C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:10]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

7

Reactant 5

HCID 284Formic AcidHCID 6342AcetonitrileHCID 2723840Benzenesulfinic acid, sodium saltHCID 115721302-(3-(Benzyloxy)phenyl)acetaldehydeHCID 21252905Tert-butylcarbamate

Product 1

HCID 11634138[1-Benzenesulfonyl-2-(3-benzyloxy-phenyl)-ethyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of (3-Benzyloxy-phenyl)-acetaldehyde (20.6 g, 91 mmol), tert-butylcarbamate (10.7 g, 91 mmol, 1 eq), sodium benzenesulfinate (18.3 g, 109 mmol, 1.2 eq) and formic acid (5.2 ml, 137 mmol, 1.5 eq) in 155 ml acetonitrile is stirred at 80° C. for 4 h. After cooling to rt the mixture is taken up in EtOAc. The solution is washed with bicarbonate and brine, dried over magnesium sulfate and evaporated. The residue (37.3 g) is used for the next step without further purification.

Workup

  1. temperatureAfter cooling to rt the mixture
  2. washThe solution is washed with bicarbonate and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue (37.3 g) is used for the next step without further purification

Sources & evidence

ORD record
ord-ea4ae68c8f8b41d7b9ec13c40987823f
Source dataset
uspto-grants-2009_11
Patent number
US07612054B2

Reaction notes

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