HCID 68839874, compound → HCID 68838865, compound

HRID 660812Notes

Reaction equation

HRID 660812 reaction equation
[CH3:1][O:2][C:3](=[O:40])[CH2:4][N:5]([S:29](=[O:39])(=[O:38])[NH:30]C(OC(C)(C)C)=O)[C:6]1[CH:11]=[CH:10][C:9]([S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:8][C:7]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:40])[CH2:4][N:5]([S:29](=[O:38])(=[O:39])[NH2:30])[C:6]1[CH:11]=[CH:10][C:9]([S:12]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)(=[O:14])=[O:13])=[CH:8][C:7]=1[O:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

3

Reactant 1

HCID 68839874HCID 68839874, compound

Product 1

HCID 68838865HCID 68838865, compound

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of N-(t-butoxycarbonylsulfamoyl)-N-(4-benzenesulfonyl-2-benzyloxyphenyl)glycine methyl ester (620 mg, 1.05 mmol) in 10 mL TFA/CH2Cl2 (1:1) is stirred at RT for 30 min. The solvent is removed under reduced pressure and the residue is redissolved in CH2Cl2 and restripped (4×). The residual oil is chromatographed on a Biotage 40M column using CH2Cl2/EtOAc (90:10) as eluent to afford the title compound: 1H NMR (CDCl3) δ 7.87 (m, 2H), 7.72 (d, J=8.2 Hz, 1H), 7.60 (m, 2H), 7.50 (m, 3H), 7.41 (m, 5H), 5.18 (s, 2H), 4.92 (br s, 2H), 4.32 (s, 2H), 3.87 (s, 3H); MS (M−1)−=489.

Workup

  1. customThe solvent is removed under reduced pressure
  2. dissolutionthe residue is redissolved in CH2Cl2
  3. customThe residual oil is chromatographed on a Biotage 40M column

Sources & evidence

ORD record
ord-e0b9dfbc478641dbbde8b27a731b1e60
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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