1,3-DI-Boc-2-methylisothiourea → HCID 178503637, compound

HRID 2216181Notes

Reaction equation

HRID 2216181 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9](=[N:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])SC)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:20][C:21]1[CH:26]=[C:25]([CH3:27])[C:24]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([S:34]([C:37]3[CH:41]=[C:40]([C:42]([NH:44][C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])=[NH:43])[S:39][C:38]=3[S:52][CH3:53])(=[O:36])=[O:35])[CH:29]=2)=[C:23]([NH:54][C:55](=[O:72])[NH:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][O:62][C:63]2[CH:71]=[CH:70][C:66]([C:67]([OH:69])=[O:68])=[CH:65][CH:64]=2)[CH:22]=1>CC(O)=O.CO>[C:48]([O:47][C:45]([NH:44][C:42](=[NH:43])[C:40]1[S:39][C:38]([S:52][CH3:53])=[C:37]([S:34]([C:30]2[CH:29]=[C:28]([C:24]3[C:25]([CH3:27])=[CH:26][C:21]([NH:20][C:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[N:12][C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])=[CH:22][C:23]=3[NH:54][C:55](=[O:72])[NH:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][O:62][C:63]3[CH:64]=[CH:65][C:66]([C:67]([OH:69])=[O:68])=[CH:70][CH:71]=3)[CH:33]=[CH:32][CH:31]=2)(=[O:35])=[O:36])[CH:41]=1)=[O:46])([CH3:51])([CH3:49])[CH3:50]

Participants

4

Reactant 2

HCID 5466031,3-DI-Boc-2-methylisothioureaHCID 1458576194-[5-[[5-amino-3-methyl-2-[3-[5-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-2-methylsulfanylthiophen-3-yl]sulfonylphenyl]phenyl]carbamoylamino]pentoxy]benzoic acid

Product 1

HCID 178503637HCID 178503637, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 10129899Acetic acid methanolSolvent

Procedure

1,3-bis(tert-Butoxycarbonyl)-2-methyl-2-thiopseudourea (433 mg, 1.49 mmol) was added to a solution of 4-[5-(3-{4-amino-3′-[5-(tert-butoxycarbonylamino-imino-methyl)-2-methylsulfanyl-thiophene-3-sulfonyl]-6-methyl-biphenyl-2-yl}-ureido)-pentyloxy]-benzoic acid (233 mg, 0.298 mmol, Example 283: step e) in 5% AcOH/MeOH (10 mL) over 2 days at 35° C. The solvents were removed in vacuo and the residue was purified by flash chromatography (1–6% MeOH/methylene chloride) to afford the title compound as a yellow solid (70 mg, 23%). ESI-MS (m/z): Calcd. for C48H61N7O12S3: 1024.4 (M+1); found: 1024.0.

Workup

  1. customThe solvents were removed in vacuo
  2. customthe residue was purified by flash chromatography (1–6% MeOH/methylene chloride)

Sources & evidence

ORD record
ord-96ce28a05b0640749cecefacc181923a
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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