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Ammonia → HCID 69330037, compound

HRID 2299621
Notes
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Reaction equation

HRID 2299621 reaction equation
[OH:1][C:2]1[CH:38]=[CH:37][C:5]2[CH2:6][CH2:7][CH2:8][CH:9]([N:11]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:12][C@H:13]([O:22][Si:23]([CH2:28][CH3:29])([CH2:26][CH3:27])[CH2:24][CH3:25])[CH2:14][O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][C:4]=2[CH:3]=1.[N:39]1[CH:44]=CC=CC=1.ClC(OC1C=CC([N+]([O-])=O)=CC=1)=[O:47].N>ClCCl.CN(C)C1C=CN=CC=1.C(O)C.O>[O:15]([CH2:14][C@@H:13]([O:22][Si:23]([CH2:26][CH3:27])([CH2:24][CH3:25])[CH2:28][CH3:29])[CH2:12][N:11]([C:30]([O:32][C:33]([CH3:35])([CH3:34])[CH3:36])=[O:31])[CH:9]1[CH2:8][CH2:7][CH2:6][C:5]2[CH:37]=[CH:38][C:2]([O:1][C:44](=[O:47])[NH2:39])=[CH:3][C:4]=2[CH2:10]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 222AmmoniaHCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 57157362HCID 57157362, compound

Product 1

HCID 69330037HCID 69330037, compound

Reagents, catalysts & solvents 4

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 702EthanolSolvent
HCID 962WaterSolvent
HCID 6344DichloromethaneSolvent

Procedure

Under nitrogen, to a solution of N-(3-hydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)-N-[(2S)-3-phenoxy-2-(triethylsilyloxy)propyl]-tert-butoxycarbonylamine (150 mg) in dichloromethane (5 ml) were added pyridine (64 ml), 4-nitrophenyl chloroformate (116 mg) and a catalytic amount of 4-dimethylaminopyridine at 5° C. After being stirred at the same temperature for 2 hours, to this one was added about 6.8M ammonia in ethanol (0.5 ml), and the mixture was stirred at room temperature for 12 hours. The resulting mixture was pured into water, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1) to give N-[(2S)-3-phenoxy-2-(triethyl-silyloxy)propyl]-N-[3-carbamoyloxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl]-tert-butoxycarbonylamine (129 mg).

Workup

  1. customat 5° C
  2. stirringthe mixture was stirred at room temperature for 12 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-4e96b4e991bc4d8dbf6ed6f88a55dcf6
Source dataset
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06495546B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes