Ammonium Chloride → ethyl 6-[[3-amino-5-methyl-4-[3-[5-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-2-methylsulfanylthiophen-3-yl]sulfonylphenyl]phenyl]carbamoylamino]hexanoate

HRID 723217Notes

Reaction equation

HRID 723217 reaction equation
[CH2:1]([O:3][C:4](=[O:50])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11]([NH:13][C:14]1[CH:19]=[C:18]([CH3:20])[C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([S:27]([C:30]3[CH:34]=[C:33]([C:35]([NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])=[NH:36])[S:32][C:31]=3[S:45][CH3:46])(=[O:29])=[O:28])[CH:22]=2)=[C:16]([N+:47]([O-])=O)[CH:15]=1)=[O:12])[CH3:2].[NH4+].[Cl-]>CCO.[Fe]>[CH2:1]([O:3][C:4](=[O:50])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11]([NH:13][C:14]1[CH:19]=[C:18]([CH3:20])[C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([S:27]([C:30]3[CH:34]=[C:33]([C:35]([NH:37][C:38]([O:40][C:41]([CH3:42])([CH3:43])[CH3:44])=[O:39])=[NH:36])[S:32][C:31]=3[S:45][CH3:46])(=[O:29])=[O:28])[CH:22]=2)=[C:16]([NH2:47])[CH:15]=1)=[O:12])[CH3:2]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 145857706ethyl 6-[[3-methyl-4-[3-[5-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-2-methylsulfanylthiophen-3-yl]sulfonylphenyl]-5-nitrophenyl]carbamoylamino]hexanoate

Product 1

HCID 145857638ethyl 6-[[3-amino-5-methyl-4-[3-[5-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-2-methylsulfanylthiophen-3-yl]sulfonylphenyl]phenyl]carbamoylamino]hexanoateYield 99.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

6-(3-{3′-[5-(tert-Butoxycarbonylamino-imino-methyl)-2-methylsulfanyl-thiophene-3-sulfonyl]-6-methyl-2-nitro-biphenyl-4-yl}-ureido)-hexanoic acid ethyl ester (74 mg, 98.9 μmol, Example 278: step b) in EtOH (5 mL) was reduced as in Example 20: step c using Fe (28 mg, 0.50 mmol) and aqueous NH4Cl solution (50 mg, 0.93 mmol, 10 mL). The solvents were removed from the filtrate in vacuo. The crude was diluted in EtOAc and washed with water and brine. The organic layer was dried over magnesium sulfate. The solvents were removed in vacuo to yield the title compound as a brown oil (70.8 mg, quantitative). ESI-MS (m/z): Calcd. for C33H43N5O7S3: 718.2 (M+1); found: 718.1.

Workup

  1. customThe solvents were removed from the filtrate in vacuo
  2. additionThe crude was diluted in EtOAc
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-cf4dec06ea9a47b28e886eba92461529
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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