Benzoic acid, 3-(chlorosulfonyl)- → HCID 66797495, compound

HRID 386708Notes

Reaction equation

HRID 386708 reaction equation
[CH:1]1([O:7][C:8]([CH2:10][O:11][C:12](=[O:16])[CH2:13][CH2:14][NH2:15])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[S:18]([C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[C:24]([OH:26])=[O:25])(=[O:20])=[O:19].C(N(CC)C(C)C)(C)C>C(Cl)Cl>[CH:1]1([O:7][C:8]([CH2:10][O:11][C:12]([CH2:13][CH2:14][NH:15][S:18]([C:21]2[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=2)[C:24]([OH:26])=[O:25])(=[O:20])=[O:19])=[O:16])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 77641Benzoic acid, 3-(chlorosulfonyl)-HCID 81531DiisopropylethylamineHCID 66797494HCID 66797494, compound

Product 1

HCID 66797495HCID 66797495, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 3-amino-propionic acid cyclohexyloxycarbonylmethyl ester (step 2) (2.30 g, 10.03 mmol) in DCM (200 ml) at RT was treated with 3-chlorosulfonyl-benzoic acid (3.64 g, 16.50 mmol) followed by N,N-diisopropylethylamine (3.04 ml, 17.45 mmol). The resulting mixture was stirred at RT for 1 h. The reaction mixture was washed with 2N HCl (200 ml), dried over MgSO4 and concentrated in vacuo to afford the title compound; LC-MS Rt 1.34 mins; 414.2 [M+H]+, Method 2minLC_v002.

Workup

  1. washThe reaction mixture was washed with 2N HCl (200 ml)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2a158013c5fb4f2a855c5eaa40f46843
Source dataset
uspto-grants-2013_02
Patent number
US08372845B2

Reaction notes

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