Water → (S)-tert-butyl 2-((S)-1-cyano-2-(4-(3-methyl-2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)phenyl)ethylcarbamoyl)piperidine-1-carboxylate

HRID 600327Notes

Reaction equation

HRID 600327 reaction equation
[OH-].COC(NS([N+](CC)(CC)CC)(=O)=O)=O.[NH2:17][C:18](=O)[C@@H:19]([NH:38][C:39]([C@@H:41]1[CH2:46][CH2:45][CH2:44][CH2:43][N:42]1[C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])=[O:40])[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:28]=[CH:29][C:30]3[O:34][C:33](=[O:35])[N:32]([CH3:36])[C:31]=3[CH:37]=2)=[CH:23][CH:22]=1.C(N(CC)CC)C.O>ClCCl>[C:18]([C@@H:19]([NH:38][C:39]([C@@H:41]1[CH2:46][CH2:45][CH2:44][CH2:43][N:42]1[C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])=[O:40])[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:28]=[CH:29][C:30]3[O:34][C:33](=[O:35])[N:32]([CH3:36])[C:31]=3[CH:37]=2)=[CH:23][CH:22]=1)#[N:17]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 11032497(Methoxycarbonylsulfamoyl)triethylammonium hydroxideHCID 57999664(S)-tert-Butyl 2-((S)-1-amino-3-(4-(3-methyl-2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)phenyl)-1-oxopropan-2-ylcarbamoyl)piperidine-1-carboxylate

Product 1

HCID 57999653(S)-tert-butyl 2-((S)-1-cyano-2-(4-(3-methyl-2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)phenyl)ethylcarbamoyl)piperidine-1-carboxylateYield 75.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(Methoxycarbonylsulfamoyl)triethylammonium hydroxide, inner salt (137 mg) was added to a solution of (S)-tert-butyl 2-((S)-1-amino-3-(4-(3-methyl-2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)phenyl)-1-oxopropan-2-ylcarbamoyl)piperidine-1-carboxylate (120 mg) and triethylamine (0.128 ml) in dichloromethane (1 mL) and stirred for 3 h. Water was added and the mixture was extracted with DCM (3 times). The organic layers were dried over (magnesium sulfate), evaporated and purified by flash silica chromatography eluting with acetone 1:2 isohexane/acetone to give the subtitle compound (87 mg).

Workup

  1. extractionthe mixture was extracted with DCM (3 times)
  2. dry with materialThe organic layers were dried over (magnesium sulfate)
  3. customevaporated
  4. custompurified by flash silica chromatography
  5. washeluting with acetone 1:2 isohexane/acetone

Sources & evidence

ORD record
ord-06b6df2b1c114102ae46a8f3c6d2d3b9
Source dataset
uspto-grants-2011_03
Patent number
US07902181B2

Reaction notes

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