Pyridine → (S)-3-(2-benzyloxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester

HRID 1814279Notes

Reaction equation

HRID 1814279 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15](Cl)(=[O:17])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:25]([O:29][C:30](=[O:40])[CH2:31][CH:32]([NH2:39])[C:33]([N:35]([O:37][CH3:38])[CH3:36])=[O:34])([CH3:28])([CH3:27])[CH3:26]>ClCCl>[C:25]([O:29][C:30](=[O:40])[CH2:31][C@H:32]([NH:39][S:15]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:17])=[O:16])[C:33]([N:35]([O:37][CH3:38])[CH3:36])=[O:34])([CH3:26])([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 1049PyridineHCID 219624592-(Benzyloxy)benzene-1-sulfonyl chlorideHCID 865881983-amino-N-methoxy-N-methyl-succinamic acid tert-butyl ester

Product 1

HCID 86588197(S)-3-(2-benzyloxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl esterYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-benzyloxy-benzenesulfonyl chloride (3.11 g, 11 mmol) in dichloromethane (50 mL) and pyridine (2.6 mL, 3 equiv) was added 3-amino-N-methoxy-N-methyl-succinamic acid tert-butyl ester (1 equiv). The reaction stirred for 16 h and was washed with 10% sulfuric acid, water, and then brine. To give (S)-3-(2-benzyloxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester as a yellow oil (4.82 g, 92%) that was sufficiently pure for further use. 1H NMR (CDCl3) 7.88(d,1H), 7.57(d,2H), 7.40(m,3H), 7.17(d,1H), 7.03(m,2H), 5.92(d,1H), 5.25(s,2H), 4.73(bs,1H), 3.57(s,3H), 2.86(s,3H), 2.63-2.39(AB quartet, 2H), 1.40(s,9H).

Workup

  1. washwas washed with 10% sulfuric acid, water

Sources & evidence

ORD record
ord-80e2d133028d456ab5a00df1c35e598f
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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