Dichloromethane → HCID 73036438, compound

HRID 2111872Notes

Reaction equation

HRID 2111872 reaction equation
C(OC(=O)[NH:7][CH:8]([C:31](=[O:35])[N:32]([CH3:34])[CH3:33])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH:24]3[S:28][C:27](=[O:29])[NH:26][C:25]3=[O:30])=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)(C)(C)C.C(Cl)[Cl:38]>>[ClH:38].[NH2:7][CH:8]([CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH:24]3[S:28][C:27](=[O:29])[NH:26][C:25]3=[O:30])=[CH:19][CH:18]=2)=[CH:14][CH:15]=1)[C:31]([N:32]([CH3:34])[CH3:33])=[O:35]

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 76573112HCID 76573112, compound

Product 1

HCID 73036438HCID 73036438, compoundYield 73.1%

Conditions

Temperature
2.5 °C

Procedure

(1-dimethylcarbamoyl-2-{4-[4-(2,4-dioxothiazolidin-5-ylmethyl)-phenoxy]-phenyl}-ethyl)-carbamic acid tert-butyl ester (0.25 g) was dissolved in CH2Cl2 and cooled to 0-5° C. Hydrogen chloride gas was bubbled through this solution for 30 min. The excess HCl was degassed and the CH2Cl2 was removed. The residual solid was triturated with EtOAc (2×25 mL), decanted, and dried to yield the desired compound 2-amino-3-{4-[4-(2,4-dioxothiazolidin-5-ylmethyl)-phenoxy]-phenyl}-N,N-dimethylpropionamide hydrochloric acid salt as a white amorphous solid (0.16 g, 73.1%). 1H NMR (DMSO-d6): 12.05 (br, 1H), 7.26 (d, J=8.4 Hz, 2H), 7.22 (d, J=8.4 Hz, 2H), 6.96 (d, J=8.4 Hz, 2H), 6.91 (d, J=8.4 Hz, 2H), 4.90 (dd, J=9.6 and 4.4 Hz, 1H), 4.53 (br, 1H), 2.91-3.14 (m, 4H), 2.81 (s, 3H), 3.05 (s, 3H).

Workup

  1. customHydrogen chloride gas was bubbled through this solution for 30 min
  2. customThe excess HCl was degassed
  3. customthe CH2Cl2 was removed
  4. customThe residual solid was triturated with EtOAc (2×25 mL)
  5. customdecanted
  6. customdried

Sources & evidence

ORD record
ord-05f1ce671aec42afba8e5b131a998e41
Source dataset
uspto-grants-2009_04
Patent number
US07521465B2

Reaction notes

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