Lithium Hydroxide → 6-[[3-(4-carboxybutanoylamino)-5-methyl-4-[3-[5-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-2-methylsulfanylthiophen-3-yl]sulfonylphenyl]phenyl]carbamoylamino]hexanoic acid

HRID 2216174Notes

Reaction equation

HRID 2216174 reaction equation
[OH-].[Li+].C([O:5][C:6](=[O:59])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]([NH:15][C:16]1[CH:21]=[C:20]([CH3:22])[C:19]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([S:29]([C:32]3[CH:36]=[C:35]([C:37]([NH:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])=[NH:38])[S:34][C:33]=3[S:47][CH3:48])(=[O:31])=[O:30])[CH:24]=2)=[C:18]([NH:49][C:50](=[O:58])[CH2:51][CH2:52][CH2:53][C:54]([O:56]C)=[O:55])[CH:17]=1)=[O:14])C>CO.O>[C:43]([O:42][C:40]([NH:39][C:37](=[NH:38])[C:35]1[S:34][C:33]([S:47][CH3:48])=[C:32]([S:29]([C:25]2[CH:24]=[C:23]([C:19]3[C:20]([CH3:22])=[CH:21][C:16]([NH:15][C:13](=[O:14])[NH:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]([OH:59])=[O:5])=[CH:17][C:18]=3[NH:49][C:50](=[O:58])[CH2:51][CH2:52][CH2:53][C:54]([OH:56])=[O:55])[CH:28]=[CH:27][CH:26]=2)(=[O:30])=[O:31])[CH:36]=1)=[O:41])([CH3:46])([CH3:44])[CH3:45]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 145857701ethyl 6-[[3-[(5-methoxy-5-oxopentanoyl)amino]-5-methyl-4-[3-[5-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-2-methylsulfanylthiophen-3-yl]sulfonylphenyl]phenyl]carbamoylamino]hexanoate

Product 1

HCID 1458576346-[[3-(4-carboxybutanoylamino)-5-methyl-4-[3-[5-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-2-methylsulfanylthiophen-3-yl]sulfonylphenyl]phenyl]carbamoylamino]hexanoic acidYield 115.6%

Reagents, catalysts & solvents 1

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

Procedure

Lithium hydroxide (53.8 μL, 0.215 mmol, 4N aqueous) was added to a solution of 6-{3-[3′-[5-(tert-butoxycarbonylamino-imino-methyl)-2-methylsulfanyl-thiophene-3-sulfonyl]-2-(4-methoxycarbonyl-butyrylamino)-6-methyl-biphenyl-4-yl]-ureido}-hexanoic acid ethyl ester (45.5 mg, 53.8 μmol, Example 278: step d) in MeOH/H2O (10 mL, 2:1) at 0° C. The reaction mixture was warmed to rt and stirred overnight. The solvents were removed in vacuo to afford the title compound as a yellow solid (50 mg, quantitative). ESI-MS (m/z): Calcd. for C36H45N5O1OS3: 804.2 (M+1); found: 803.9.

Workup

  1. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-755ae908b55c42f8b001e2201997c200
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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