Sodium Hydroxide → HCID 145857659, compound

HRID 723163Notes

Reaction equation

HRID 723163 reaction equation
C[O:2][C:3](=[O:48])[CH2:4][NH:5][C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12]([NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:16]=1[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([S:28]([C:31]2[CH:35]=[C:34]([C:36]([NH:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])=[NH:37])[S:33][C:32]=2[S:46][CH3:47])(=[O:30])=[O:29])[CH:23]=1)=[O:13])=[O:7].[OH-].[Na+]>CO.O>[C:42]([O:41][C:39]([NH:38][C:36](=[NH:37])[C:34]1[S:33][C:32]([S:46][CH3:47])=[C:31]([S:28]([C:24]2[CH:23]=[C:22]([C:16]3[C:17]([CH3:21])=[CH:18][CH:19]=[CH:20][C:15]=3[NH:14][C:12](=[O:13])[NH:11][CH2:10][CH2:9][NH:8][C:6](=[O:7])[NH:5][CH2:4][C:3]([OH:48])=[O:2])[CH:27]=[CH:26][CH:25]=2)(=[O:30])=[O:29])[CH:35]=1)=[O:40])([CH3:45])([CH3:43])[CH3:44]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 145857606HCID 145857606, compound

Product 1

HCID 145857659HCID 145857659, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of {3-[2-(3-{3′-[5-(tert-butoxycarbonylamino-imino-methyl)-2-methylsulfanyl-thiophene-3-sulfonyl]-6-methyl-biphenyl-2-yl}-ureido)-ethyl]-ureido}-acetic acid methyl ester ((Example 197: step a) 0.031 g, 0.042 mmol) in MeOH:water (2:1, 15 mL) was treated with NaOH (10 N, 0.042 mL, 0.420 mmol) and stirred at room temperature 18 h. MeOH was evaporated in vacuo and the remaining aqueous solution was acidified to pH 5 with glacial acetic acid. The solution was extracted with CH2Cl2 (3×50 mL). The combined organic layers were dried over MgSO4 and evaporated in vacuo to afford the product {3-[2-(3-{3′-[5-(tert-butoxycarbonylamino-imino-methyl)-2-methylsulfanyl-thiophene-3-sulfonyl]-6-methyl-biphenyl-2-yl}-ureido)-ethyl]-ureido}-acetic acid (0.025 g, 83%) as an off-white solid. The crude material was used directly in the next reaction.

Workup

  1. customMeOH was evaporated in vacuo
  2. extractionThe solution was extracted with CH2Cl2 (3×50 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-a1d3d42bdbc84287b5bd0513eacc91f9
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

Loading…