1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 67140081, compound

HRID 1592009Notes

Reaction equation

COC1C=C(OC)C=CC=1C[N:6]1[S:10](=[O:12])(=[O:11])[N:9]([CH2:13][C:14]2[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=2)[CH2:8][C:7]1=[O:23].[C:30]([O:34][C:35](=[O:44])[C:36]1[CH:41]=[CH:40][C:39]([CH2:42]O)=[CH:38][CH:37]=1)([CH3:33])([CH3:32])[CH3:31].CCN=C=NCCCN(C)C.Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:30]([O:34][C:35]([C:36]1[CH:41]=[CH:40][C:39]([CH2:42][O:20][C:18](=[O:19])[C:17]2[CH:16]=[CH:15][C:14]([CH2:13][N:9]3[CH2:8][C:7](=[O:23])[NH:6][S:10]3(=[O:11])=[O:12])=[CH:22][CH:21]=2)=[CH:38][CH:37]=1)=[O:44])([CH3:33])([CH3:31])[CH3:32]

Participants

Conditions

Temperature: 5 °C

Procedure

A solution of the title B compound, 4-[5-(2,4-dimethoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-ylmethyl]-benzoic acid (84 mg, 0.2 mmol) and 4-hydroxymethyl-benzoic acid t-butyl ester (42 mg, 0.2 mmol) in CH2Cl2 (3 mL) is treated with DMAP (12 mg, 0.1 mmol) and the reaction is cooled to 5° C. EDCl (39 mg, 0.2 mmol) is then added and the reaction is stirred for 16 h. The mixture is concentrated and partioned between EtOAc and 1N aqueous HCl. The organic solution is washed with saturated aqueous NaHCO3 and brine, dried over anhydrous MgSO4 and concentrated to give 4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-ylmethyl)-benzoic acid 4-t-butoxycarbonyl-benzyl ester as a white solid.

Workup

concentrationThe mixture is concentrated
washThe organic solution is washed with saturated aqueous NaHCO3 and brine
dry with materialdried over anhydrous MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-3a8080ab36f840b798a2e80aece7f06c
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07291635B2

Reaction notes

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