HCID 59532380, compound → HCID 59532367, compound

HRID 450983Notes

Reaction equation

HRID 450983 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C@@H:14]([N:16]3[CH2:21][CH2:20][C@:19]([CH2:27][C:28](O)=[O:29])([C:22]4[S:23][CH:24]=[CH:25][CH:26]=4)[O:18][C:17]3=[O:31])[CH3:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C@@H:14]([N:16]3[CH2:21][CH2:20][C@:19]([CH2:27][CH2:28][OH:29])([C:22]4[S:23][CH:24]=[CH:25][CH:26]=4)[O:18][C:17]3=[O:31])[CH3:15])=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 59532380HCID 59532380, compound

Product 1

HCID 59532367HCID 59532367, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-((S)-3-((S)-1-(4′-fluorobiphenyl-4-yl)ethyl)-2-oxo-6-(thiophen-2-yl)-1,3-oxazinan-6-yl)acetic acid (218 mg, 0.5 mmol) in THF anhydrous (10 mL) was added BH3 (3.0 mL) at 0 and then stirred at reflux for 2 h. Then the reaction mixture quenched by water and separated, extracted with EtOAc twice. The organic phases was dried over Na2SO4, filtered and concentrated to afford the residue, which was purified by TLC to give (S)-3-((S)-1-(4′-fluorobiphenyl-4-yl)ethyl)-6-(2-hydroxyethyl)-6-(thiophen-2-yl)-1,3-oxazinan-2-one (85 mg, 40%). LC-MS Method 3 tR=1.35, min, m/z=426, 448; 1H NMR (CD3OD): 1.50 (m, 3H), 2.15 (m, 2H), 2.30 (m, 1H), 2.40 (m, 1H), 2.60 (m, 1H), 3.15 (m, 1H), 3.45 (m, 1H), 3.70 (m, 1H), 5.60 (m, 1H), 6.90 (m, 1H), 7.00 (m, 1H), 7.10 (m, 4H), 7.35 (m, 3H), 7.55 (m, 2H).

Workup

  1. temperatureat reflux for 2 h
  2. customThen the reaction mixture quenched by water
  3. customseparated
  4. extractionextracted with EtOAc twice
  5. dry with materialThe organic phases was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford the residue, which
  9. customwas purified by TLC

Sources & evidence

ORD record
ord-e42cc281166644738696b2e23a2c4085
Source dataset
uspto-grants-2013_07
Patent number
US08487094B2

Reaction notes

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