Hydrochloric Acid → HCID 73775593, compound

HRID 530603Notes

Reaction equation

HRID 530603 reaction equation
[CH2:1]([C@@H:8]1[O:13][CH2:12][CH2:11][N:10]([CH2:14][C@H:15]([O:20][C:21](=[O:30])[NH:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[C:16]([F:19])([F:18])[F:17])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.CCCCCC>CCOCC>[ClH:29].[CH2:1]([C@@H:8]1[O:13][CH2:12][CH2:11][N:10]([CH2:14][C@H:15]([O:20][C:21](=[O:30])[NH:22][C:23]2[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=2)[C:16]([F:17])([F:18])[F:19])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 73775594HCID 73775594, compound

Product 1

HCID 73775593HCID 73775593, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

The crude reaction mixture was concentrated in vacuo, dissolved in dichloromethane and methanol and silica was added. The suspension was concentrated in vacuo. The resulting residue was dry-loaded onto a 40 g column. Flash chromatography (90/10 hexanes/ethyl acetate) afforded the late-running spot, assigned as (4-chloro-phenyl)-carbamic acid (S)-1-((S)-2-benzyl-morpholin-4-ylmethyl)-2,2,2-trifluoro-ethyl ester, as a white foam. The resulting white foam was dissolved in ether and 0.5 mL of 1 M HCl in ether was added. Hexane was added to the resulting suspension and the solid was washed with ether/hexanes and dried under vacuum to yield (4-chloro-phenyl)-carbamic acid (S)-1-((S)-2-benzyl-morpholin-4-ylmethyl)-2,2,2-trifluoro-ethyl ester hydrochloride (242 mg, 24%) as an off-white solid. (M+H)+=443 m/e.

Workup

  1. washthe solid was washed with ether/hexanes
  2. customdried under vacuum

Sources & evidence

ORD record
ord-de7f636105ee43e7ba3e04fdbb331745
Source dataset
uspto-grants-2016_05
Patent number
US09353096B2

Reaction notes

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