Triethylamine → HCID 86673855, compound

HRID 1527427Notes

Reaction equation

HRID 1527427 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:13]([C:14](=[O:25])[NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:18]=2[F:24])[CH2:12][C@:11]2([CH2:26][OH:27])[C@H:9]1[CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[CH3:35][S:36](Cl)(=[O:38])=[O:37].C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[C@H:13]([C:14](=[O:25])[NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:18]=2[F:24])[CH2:12][C@:11]2([CH2:26][O:27][S:36]([CH3:35])(=[O:38])=[O:37])[C@H:9]1[CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 516892Sodium BicarbonateHCID 68283738HCID 68283738, compound

Product 1

HCID 86673855HCID 86673855, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1R,3S,5S)-3-(3-chloro-2-fluoro-benzylcarbamoyl)-5-hydroxymethyl-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester (290 mg, 0.72 mmol) and Et3N (144 μL, 1.04 mmol) in CH2Cl2 (6.5 mL) at 0° C. under nitrogen atmosphere was added methanesulfonyl chloride (81 μL, 1.04 mmol) and the mixture was stirred at RT for 1 h. Et3N (48 μL, 0.35 mmol) and methanesulfonyl chloride (27 μL, 0.35 mmol) were again added and the mixture was further stirred for 0.5 h to complete the reaction. A saturated aqueous solution of NaHCO3 was added, the layers were separated and the aqueous layer extracted with CH2Cl2 (×2), dried (Na2SO4), filtered and concentrated. The material thus obtained was used in the next step without further purification. TLC, Rf (EtOAc)=0.65; MS (UPLC/MS): 477.3/479.3 [M+H]+, 521.3/523.3 [M+HCOO]—

Workup

  1. stirringthe mixture was further stirred for 0.5 h
  2. customthe reaction
  3. customthe layers were separated
  4. extractionthe aqueous layer extracted with CH2Cl2 (×2)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe material thus obtained
  9. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-392f19123c4849cda3e9db72f51795b8
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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