Lithium Hydroxide → 3-[3-methyl-2-[3-[5-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-2-methylsulfanylthiophen-3-yl]sulfonylphenyl]anilino]-3-oxopropanoic acid

HRID 2216047Notes

Reaction equation

HRID 2216047 reaction equation
C[O:2][C:3](=[O:41])[CH2:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:9]=1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([S:21]([C:24]2[CH:28]=[C:27]([C:29]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[NH:30])[S:26][C:25]=2[S:39][CH3:40])(=[O:23])=[O:22])[CH:16]=1)=[O:6].[OH-].[Na+].[Li+].[OH-]>CO>[C:35]([O:34][C:32]([NH:31][C:29](=[NH:30])[C:27]1[S:26][C:25]([S:39][CH3:40])=[C:24]([S:21]([C:17]2[CH:16]=[C:15]([C:9]3[C:10]([CH3:14])=[CH:11][CH:12]=[CH:13][C:8]=3[NH:7][C:5](=[O:6])[CH2:4][C:3]([OH:41])=[O:2])[CH:20]=[CH:19][CH:18]=2)(=[O:23])=[O:22])[CH:28]=1)=[O:33])([CH3:38])([CH3:36])[CH3:37]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 14798Sodium HydroxideHCID 145857671methyl 3-[3-methyl-2-[3-[5-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-2-methylsulfanylthiophen-3-yl]sulfonylphenyl]anilino]-3-oxopropanoate

Product 1

HCID 1458576393-[3-methyl-2-[3-[5-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-2-methylsulfanylthiophen-3-yl]sulfonylphenyl]anilino]-3-oxopropanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-{3′-[5-(tert-Butoxycarbonylamino-imino-methyl)-2-methylsulfanyl-thiophene-3-sulfonyl]-6-methyl-biphenyl-2-yl}-malonamic acid methyl ester (20 mg, 0.03 mmol, Example 132: step a) and NaOH (1M, 90 μL, 0.09 mmol) were dissolved into MeOH (1.5 mL). The reaction was stirred for 2 hours. LiOH (1.0 mg, 0.05 mmol) was added and the reaction was stirred at RT overnight. The solvents were removed in vacuo and used with out further purification in the next step. ESI-MS (m/z): Calcd. for C27H29N3O7S3: 604.1 (M+1); found: 504.0 (loss of boc).

Workup

  1. stirringthe reaction was stirred at RT overnight
  2. customThe solvents were removed in vacuo
  3. customused with out further purification in the next step

Sources & evidence

ORD record
ord-53529758fcb647e3a9c67158ab0b8446
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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