Hydrochloric Acid → HCID 11669598, compound

HRID 20479Notes

Reaction equation

HRID 20479 reaction equation
[NH2:1][C@@H:2]([CH2:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[C:21]([F:26])[CH:20]=1)[C@@H:3]([C@H:5]1[CH2:10][O:9][C@@H:8]([O:11][CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C@H:7]([CH3:17])[NH:6]1)[OH:4].[C:27](OC(=O)C)(=[O:29])[CH3:28].[ClH:34]>C(OCC)C.C1C=CC=CC=1>[ClH:34].[F:26][C:21]1[CH:20]=[C:19]([CH:24]=[C:23]([F:25])[CH:22]=1)[CH2:18][C@H:2]([NH:1][C:27](=[O:29])[CH3:28])[C@@H:3]([C@H:5]1[CH2:10][O:9][C@@H:8]([O:11][CH2:12][C:13]([CH3:15])([CH3:16])[CH3:14])[C@H:7]([CH3:17])[NH:6]1)[OH:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 58972243HCID 58972243, compound

Product 1

HCID 11669598HCID 11669598, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

Dissolve (1S,2S)-2-amino-3-(3,5-difluorophenyl)-1-[(3R,5S,6R)-6-(2,2-dimethylpropoxy)-5-methylmorpholin-3-yl]-propan-1-ol (70 mg, 0.188 mmol) in dry dichloromnethane (1.8 mL) under nitrogen. Add dropwise acetic anhydride (22 μL, 0.233 mmol) and stir for 1 hour. Add 1 M hydrogen chloride in diethyl ether (1 mL) and dilute with benzene. Concentrate and purify (HPLC, eluting with 30% to 70% acetonitrile with 0.1% hydrochloric acid in water) to give the title compound as a white solid (38 mg, 45%)

Workup

  1. concentrationConcentrate
  2. custompurify
  3. wash(HPLC, eluting with 30% to 70% acetonitrile with 0.1% hydrochloric acid in water)

Sources & evidence

ORD record
ord-d261cb6ab1bc4a1b96d0031de532699c
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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