1,3-DI-Boc-2-methylisothiourea → HCID 178503639, compound

HRID 723189Notes

Reaction equation

HRID 723189 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].[C:20]([O:24][C:25](=[O:66])[NH:26][C:27]([C:29]1[S:30][C:31]([S:64][CH3:65])=[C:32]([S:34]([C:37]2[CH:38]=[C:39]([C:43]3[C:48]([CH3:49])=[CH:47][C:46]([NH2:50])=[CH:45][C:44]=3[NH:51][C:52]([NH:54][CH2:55][CH2:56][NH:57][C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)=[O:53])[CH:40]=[CH:41][CH:42]=2)(=[O:36])=[O:35])[CH:33]=1)=[NH:28])([CH3:23])([CH3:22])[CH3:21]>CO.C(O)(=O)C>[C:20]([O:24][C:25](=[O:66])[NH:26][C:27]([C:29]1[S:30][C:31]([S:64][CH3:65])=[C:32]([S:34]([C:37]2[CH:38]=[C:39]([C:43]3[C:48]([CH3:49])=[CH:47][C:46]([NH:50][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:45][C:44]=3[NH:51][C:52]([NH:54][CH2:55][CH2:56][NH:57][C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)=[O:53])[CH:40]=[CH:41][CH:42]=2)(=[O:35])=[O:36])[CH:33]=1)=[NH:28])([CH3:22])([CH3:23])[CH3:21]

Participants

5

Reactant 2

HCID 5466031,3-DI-Boc-2-methylisothioureaHCID 145857703HCID 145857703, compound

Product 1

HCID 178503639HCID 178503639, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

1,3-Bis-t-butoxycarbonyl-2-methyl-2-thiopseudourea (0.033 g, 0.114 mmol) was added to a solution of [(4-{4′-amino-6′-methyl-2′-[3-(2-phenylamino-ethyl)-ureido]-biphenyl-3-sulfonyl}-5-methylsulfanyl-thiophen-2-yl)-imino-methyl]-carbamic acid tert-butyl ester [example 216, step a] in methanol [1 mL] and 1 drop of acetic acid. The reaction was stirred at room temperature for 1 hour and evaporated. The reaction was evaporated and column chromatography (25% EtOAc in hexanes) of the residue yielded the title compound (0.072 g, 68%) as a solid. ESI-MS (m/z): Calcd. for C44H56N8O9S3: 936.33; found: 936.9.

Workup

  1. customevaporated
  2. customThe reaction was evaporated

Sources & evidence

ORD record
ord-f748d7eb8be646dba85cacec50e2f11f
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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