1-Hydroxybenzotriazole → HCID 69584746, compound

HRID 1825757Notes

Reaction equation

HRID 1825757 reaction equation
[C:1]([O:5][C:6](=[O:24])[N:7]([C@@H:18]1[CH2:22][CH2:21][CH2:20][C@H:19]1[NH2:23])[CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:25][S:26]([C:29]1[CH:37]=[CH:36][C:32]([C:33](O)=[O:34])=[CH:31][CH:30]=1)(=[O:28])=[O:27].C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:24])[N:7]([CH2:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=1)[C@@H:18]1[CH2:22][CH2:21][CH2:20][C@H:19]1[NH:23][C:33](=[O:34])[C:32]1[CH:31]=[CH:30][C:29]([S:26]([CH3:25])(=[O:28])=[O:27])=[CH:37][CH:36]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 77670p-(Methylsulphonyl)benzoic acidHCID 58633708HCID 58633708, compound

Product 1

HCID 69584746HCID 69584746, compoundYield 106.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using General Procedure C, (±)-trans-(2-aminocyclopentyl)-[3-(4-chloro-phenyl)propyl]carbamic acid tert-butyl ester (155 mg, 0.44 mmol) and 4-methanesulfonylbenzoic acid (105 mg, 0.53 mmol) were coupled in CH2Cl2 (3 mL) using HOBt (12 mg, 0.09 mmol) and DEC (106 mg, 0.66 mmol) at 0° C. for 2.5 hours to give 250 mg of (±)-trans-[3-(4-chlorophenyl)propyl]-[2-(4-methanesulfonylbenzoylamino)cyclopentyl]carbamic acid tert-butyl ester as a colorless oil.

Workup

  1. customat 0° C.
  2. customfor 2.5 hours

Sources & evidence

ORD record
ord-38e7f37bfd684b978b2298cf515effed
Source dataset
uspto-grants-2006_05
Patent number
US07049317B2

Reaction notes

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