Diisopropylethylamine → HCID 131725921, compound

HRID 2212252Notes

Reaction equation

HRID 2212252 reaction equation
C1(NC(N[S:10]([CH3:13])(=[O:12])=[O:11])=S)CCCC1.[NH2:14][CH:15]([CH2:33][S:34]([CH2:37][CH:38]1[CH2:40][CH2:39]1)(=[O:36])=[O:35])[C:16]([NH:18][CH:19]([CH:22]([C:24]1[O:25][C:26]2[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=2[N:28]=1)[OH:23])[CH2:20][CH3:21])=[O:17].[I-].[CH3:42][N+:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1Cl.[CH3:50]CN(C(C)C)C(C)C>ClCCl.C(OCC)(=O)C>[O:25]1[C:26]2[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=2[N:28]=[C:24]1[CH:22]([OH:23])[CH:19]([NH:18][C:16](=[O:17])[CH:15]([NH:14][C:42]([NH:43][CH:48]1[CH2:47][CH2:46][CH2:45][CH2:44]1)=[CH:50][S:10]([CH3:13])(=[O:12])=[O:11])[CH2:33][S:34]([CH2:37][CH:38]1[CH2:40][CH2:39]1)(=[O:35])=[O:36])[CH2:20][CH3:21]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 21962730HCID 21962730, compoundHCID 69616468HCID 69616468, compound

Product 1

HCID 131725921HCID 131725921, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 1-cyclopentyl-3-methylsulfonylthiourea (200 mg, 0.89 mmol, 2.4 equiv.), 2-amino-N-[1-(benzoxazol-2-ylhydroxymethyl)-propyl]-3-cyclopropylmethanesulfonyl-propionamide (163 mg, 1.0 equiv.), N-methyl-2-chloropyridinium iodide (175 mg, 1.8 equiv.) in 4 mL dichloromethane was added DIPEA (142 mg, 2.8 equiv). The reaction mixture was stirred overnight at ambient temp. The reaction was diluted with ethyl acetate and extracted with saturated sodium bicarbonate, brine and dried over MgSO4. Purification by column chromatography (EtOAC/hexanes) afforded N-[1-(benzoxazol-2-ylhydroxymethyl)propyl]-2-(1-cyclopentylamino-2-methanesulfonylvinylamino)-3-cyclopropylmetanesulfonylpropionamide as a mixture of diastereomers (41 mg, M=584.3 M+1) which was oxidized to the title compound using Dess-Martin Periodane as previously described.

Workup

  1. extractionextracted with saturated sodium bicarbonate, brine
  2. dry with materialdried over MgSO4
  3. customPurification by column chromatography (EtOAC/hexanes)

Sources & evidence

ORD record
ord-71cd61756eca466891600cba45894a80
Source dataset
uspto-grants-2006_09
Patent number
US07101880B2

Reaction notes

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