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 2216172Notes

Reaction equation

HRID 2216172 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]hexanoate

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, 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-c950dacc14304beeb5746a60b3eed5a3
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

Loading…