Lithium Hydroxide → HCID 145857622, compound

HRID 723205Notes

Reaction equation

HRID 723205 reaction equation
C([O:3][C:4](=[O:57])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11]([NH:13][C:14]1[CH:19]=[C:18]([NH:20][C:21]([O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])=[O:22])[CH:17]=[C:16]([CH3:30])[C:15]=1[C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([S:37]([C:40]2[CH:44]=[C:43]([C:45]([NH:47][C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])=[NH:46])[S:42][C:41]=2[S:55][CH3:56])(=[O:39])=[O:38])[CH:32]=1)=[O:12])C.[Li+].[OH-]>C1COCC1.O>[C:51]([O:50][C:48]([NH:47][C:45](=[NH:46])[C:43]1[S:42][C:41]([S:55][CH3:56])=[C:40]([S:37]([C:33]2[CH:32]=[C:31]([C:15]3[C:16]([CH3:30])=[CH:17][C:18]([NH:20][C:21]([O:23][CH2:24][CH2:25][Si:26]([CH3:27])([CH3:29])[CH3:28])=[O:22])=[CH:19][C:14]=3[NH:13][C:11](=[O:12])[NH:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]([OH:57])=[O:3])[CH:36]=[CH:35][CH:34]=2)(=[O:39])=[O:38])[CH:44]=1)=[O:49])([CH3:54])([CH3:52])[CH3:53]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 145857604HCID 145857604, compound

Product 1

HCID 145857622HCID 145857622, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of 6-{3-[3′-[5-(tert-butoxycarbonylamino-imino-methyl)-2-methylsulfanyl-thiophene-3-sulfonyl]-6-methyl-4-(2-trimethylsilanyl-ethoxycarbonylamino)-biphenyl-2-yl]-ureido}-hexanoic acid ethyl ester ((Example 259: step a) 0.437 g, 0.507 mmol) in THF:water (2:1, 15 mL) was treated with solid LiOH (0.097 g, 4.06 mmol) and stirred at room temperature 18.5 h. The THF was removed 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 concentrated in vacuo to afford the title compound (0.4222 g, 99%) as an off-white solid. ESI-MS (m/z): Calcd. for C37H51N5O9S3Si (M+H): 834.3; 834.2.

Workup

  1. customThe THF was removed in vacuo
  2. extractionThe solution was extracted with CH2Cl2 (3×50 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8a628473f44a4441b863ebea062ebbc5
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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