Dichloromethane → HCID 178501015, compound

HRID 723154Notes

Reaction equation

HRID 723154 reaction equation
[C:1]([O:5][C:6](=[O:43])[NH:7][C:8]([C:10]1[S:11][C:12]([S:41][CH3:42])=[C:13]([S:15]([C:18]2[CH:39]=[C:38]([Br:40])[C:21]3[N:22]=[CH:23][N:24]([CH2:25][C:26]4[CH:31]=[C:30]([NH:32][C:33](=[O:36])CBr)[CH:29]=[CH:28][C:27]=4[F:37])[C:20]=3[CH:19]=2)(=[O:17])=[O:16])[CH:14]=1)=[NH:9])([CH3:4])([CH3:3])[CH3:2].[SH:44][CH2:45][CH2:46][C:47]([O:49][CH3:50])=[O:48].[CH2:51](Cl)Cl>>[CH3:50][O:49][C:47](=[O:48])[CH2:46][CH2:45][SH:44]([C:33](=[O:36])[NH:32][C:30]1[CH:29]=[CH:28][C:27]([F:37])=[C:26]([CH2:25][N:24]2[C:20]3[CH:19]=[C:18]([S:15]([C:13]4[CH:14]=[C:10]([C:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:43])=[NH:9])[S:11][C:12]=4[S:41][CH3:42])(=[O:16])=[O:17])[CH:39]=[C:38]([Br:40])[C:21]=3[N:22]=[CH:23]2)[CH:31]=1)[CH3:51]

Participants

4

Reactant 3

HCID 6344Dichloromethane2×HCID 18050Methyl 3-mercaptopropionateHCID 145857713HCID 145857713, compound

Product 1

HCID 178501015HCID 178501015, compoundYield 85%

Procedure

A solution of [(4-{7-bromo-3-[5-(2-bromo-acetylamino)-2-fluoro-benzyl]-3H-benzoimidazole-5-sulfonyl}-5-methylsulfanyl-thiophen-2-yl)-imino-methyl]-carbamic acid tert-butyl ester ((Example 191: step a) 0.014 g, 0.017 mmol) in CH2Cl2 (2 mL) was treated with methyl 3-mercaptopropionoate (2.50 μL, 0.025 mmol) and stirred at room temperature 30 min. The reaction was diluted with CH2Cl2 and washed with water (1×10 mL). The organic layer was dried over MgSO4 and concentrated in vacuo to afford the product 3-[(3-{4-bromo-6-[5-(tert-butoxycarbonylamino-imino-methyl)-2-methylsulfanyl-thiophene-3-sulfonyl]-benzoimidazol-1-ylmethyl}-4-fluoro-phenylcarbamoyl)-methylsulfanyl]-propionic acid methyl ester (0.011, 85%) as a tan solid. C31H33BrFN5O8S4: 814.04 (M+1) found 814.70.

Workup

  1. washwashed with water (1×10 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-010418bad56d4b2f8b4b06d1b2aec045
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

Loading…