Acetic Acid → HCID 9831862, compound

HRID 1741671Notes

Reaction equation

HRID 1741671 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([NH:22][C:23]([O:25][CH:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)=[O:24])[CH:20]=2)[N:15]([CH2:31][C:32]2[CH:41]=[CH:40][C:39]3[C:34](=[CH:35][C:36]([Cl:42])=[CH:37][CH:38]=3)[N:33]=2)[CH:14]=1)[C:6](O)=[O:7].[CH3:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=1[S:50]([NH2:53])(=[O:52])=[O:51].Cl.CN(C)CCCN=C=NCC.CC(O)=O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([NH:22][C:23]([O:25][CH:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)=[O:24])[CH:20]=2)[N:15]([CH2:31][C:32]2[CH:41]=[CH:40][C:39]3[C:34](=[CH:35][C:36]([Cl:42])=[CH:37][CH:38]=3)[N:33]=2)[CH:14]=1)[C:6]([NH:53][S:50]([C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][C:44]=1[CH3:43])(=[O:52])=[O:51])=[O:7]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 69242-MethylbenzenesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19010466HCID 19010466, compound

Product 1

HCID 9831862HCID 9831862, compoundYield 85.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution the acid from Step 4 (159 mg) and 2-methylbenzenesulfonamide (70 mg) in CH2Cl2 (3 ml) was added successively 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (78 mg) and DMAP (50 mg). After stirring at r.t. overnight, HOAc (200 μl) was added and the mixture was concentrated. Chromatography of the residue using EtOAc/hexane (2:3) containing 1% HOAc afforded 172 mg of the title compound.

Workup

  1. concentrationthe mixture was concentrated
  2. additioncontaining 1% HOAc

Sources & evidence

ORD record
ord-fa1e85179edc4b738d30792bf0a6c8a0
Source dataset
uspto-grants-1994_08
Patent number
US05334597

Reaction notes

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