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Water → Tert-butyl 3-(3-chloro-5-(1-chloroethyl)-2-fluoro-6-methoxyphenyl)azetidine-1-carboxylate

HRID 510946
Notes
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Reaction equation

HRID 510946 reaction equation
N1C(Cl)=NC(Cl)=NC=1[Cl:3].CN(C=O)C.[Cl:15][C:16]1[C:17]([F:38])=[C:18]([CH:27]2[CH2:30][N:29]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:28]2)[C:19]([O:25][CH3:26])=[C:20]([CH:22](O)[CH3:23])[CH:21]=1.O>ClCCl>[Cl:15][C:16]1[C:17]([F:38])=[C:18]([CH:27]2[CH2:30][N:29]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:28]2)[C:19]([O:25][CH3:26])=[C:20]([CH:22]([Cl:3])[CH3:23])[CH:21]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 7954Cyanuric chlorideHCID 86666860Tert-butyl 3-(3-chloro-2-fluoro-5-(1-hydroxyethyl)-6-methoxyphenyl)azetidine-1-carboxylate

Product 1

HCID 86666861Tert-butyl 3-(3-chloro-5-(1-chloroethyl)-2-fluoro-6-methoxyphenyl)azetidine-1-carboxylateYield 53.2%

Reagents, catalysts & solvents

1
HCID 6344DichloromethaneSolvent2×

Procedure

Cyanuric chloride (140 mg, 0.78 mmol) was added to DMF (0.059 mL, 0.77 mmol) at room temperature. After the formation of a white solid (10 min), methylene chloride (4 mL) was added, followed by tert-butyl 3-[3-chloro-2-fluoro-5-(1-hydroxyethyl)-6-methoxyphenyl]azetidine-1-carboxylate (197 mg, 0.547 mmol). After the addition, the mixture was stirred at room temperature overnight. Water was added, and the resulting mixture was then diluted with dichloromethane. The organic phase was separated, washed with sat. NaHCO3 solution, water and brine, dried over MgSO4, concentrated and purified on silica gel (eluting with 0 to 30% EtOAc in hexanes) to give the desired product (110 mg, 53%).

Workup

  1. additionAfter the addition
  2. customThe organic phase was separated
  3. washwashed with sat. NaHCO3 solution, water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. custompurified on silica gel (eluting with 0 to 30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-0bd0d5a79a07465ca82d1b43eeaf90c4
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09096600B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes