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Sodium hydride → 4-Benzyl 1,4-di-tert-butyl (1S)-5-[5-(benzyloxy)pyridin-2-yl]-1-[(tert-butoxycarbonyl)amino]pentane-1,4,4-tricarboxylate

HRID 591303
Notes
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Reaction equation

HRID 591303 reaction equation
[CH2:1]([O:8][C:9]([CH:11]([CH2:19][CH2:20][C@H:21]([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:39]([O:46][C:47]1[CH:48]=[CH:49][C:50]([CH2:53]Br)=[N:51][CH:52]=1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>CN(C)C=O>[CH2:39]([O:46][C:47]1[CH:48]=[CH:49][C:50]([CH2:53][C:11]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:19][CH2:20][C@H:21]([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])=[N:51][CH:52]=1)[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 797999495-(Benzyloxy)-2-(bromomethyl)pyridineHCID 117812690Di-tert-butyl (5S)-2-(benzyloxycarbonyl)-5-[(tert-butoxycarbonyl)amino]hexanedioate

Product 1

HCID 1178126974-Benzyl 1,4-di-tert-butyl (1S)-5-[5-(benzyloxy)pyridin-2-yl]-1-[(tert-butoxycarbonyl)amino]pentane-1,4,4-tricarboxylateYield 65.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 360 mg of di-tert-butyl (5S)-2-(benzyloxycarbonyl)-5-[(tert-butoxy-carbonyl)amino]hexanedioate (0.71 mmol; see example 12f) in N,N-dimethyl formamide (10 mL) was added under argon atmosphere 26 mg of sodium hydride (60% in oil, 0.64 mmol). The resulting mixture was stirred at room temperature for 30 minutes. A solution of 197 mg 5-(benzyloxy)-2-(bromomethyl)pyridine (prepared according to example 17a; 0.71 mmol) in N,N-dimethylformamide (5 mL) was added, and the mixture was stirred at 60° C. for one hour. After cooling to room temperature, the mixture was concentrated in vacuo and the residue was purified by preparative HPLC (method A) to give 327 mg of the title compound (65% yield).

Workup

  1. stirringthe mixture was stirred at 60° C. for one hour
  2. temperatureAfter cooling to room temperature
  3. concentrationthe mixture was concentrated in vacuo
  4. customthe residue was purified by preparative HPLC (method A)

Sources & evidence

ORD record
ord-f314c9095a6a455185bd6e47f193a335
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09238631B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes