Sodium Bicarbonate → HCID 59598459, compound

HRID 2266291Notes

Reaction equation

HRID 2266291 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][O:7][C@@H:8]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:23]=1[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([CH3:35])[CH:30]=1)[C@@H:9]1[O:14][CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]1)(=[O:3])[CH3:2].C([O-])(O)=O.[Na+]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[F:28][C:24]1[C:23]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([CH3:35])[CH:30]=2)=[C:22]([C@@H:8]([C@@H:9]2[O:14][CH2:13][CH2:12][NH:11][CH2:10]2)[O:7][CH2:6][CH2:5][NH:4][C:1](=[O:3])[CH3:2])[CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 59598512HCID 59598512, compound

Product 1

HCID 59598459HCID 59598459, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

(R)-tert-butyl 2-((S)-(2-acetamidoethoxy)(6-fluoro-3′-methylbiphenyl-2-yl)methyl)morpholine-4-carboxylate (202 mg, 0.42 mmol) was dissolved in 20% TFA in CH2Cl2 (8 mL) and stirred for about 1 h at rt. The mixture was neutralized with satd aq NaHCO3 and the product was extracted with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated to give N-(2-((S)-(6-fluoro-3′-methylbiphenyl-2-yl)((R)-morpholin-2-yl)methoxy)ethyl)acetamide (130 mg, 82%). 1H NMR (300 MHz, CDCl3): δ=1.98 (s, 3 H), 2.39 (s, 3 H), 2.90˜3.3 (m, 6 H), 3.31˜3.41 (m, 2 H), 3.6˜4.0 (m, 3 H), 4.33 (d, 1 H), 6.56˜6.57 (s, 1 H), 6.97˜7.14 (m, 3 H), 7.27˜7.40 (m, 4 H), 9.40˜9.55 (s, 1H). MS (E/Z): 387 (M+H+).

Workup

  1. extractionthe product was extracted with CH2Cl2
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-52281f905a26420cb161d4fe9e0d6a48
Source dataset
uspto-grants-2010_12
Patent number
US07858624B2

Reaction notes

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