Ethyl Acetate → (R)-4-Phenylsulfanylmethyl-4,5-dihydro-oxazol-2-ylamine

HRID 1911540Notes

Reaction equation

HRID 1911540 reaction equation
[NH2:1][C@@H:2]([CH2:5][S:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:3][OH:4].C([O-])([O-])=O.[K+].[K+].[N:19]#[C:20]Br.C(OCC)(=O)C>C1COCC1.O>[C:7]1([S:6][CH2:5][C@H:2]2[CH2:3][O:4][C:20]([NH2:19])=[N:1]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 68714506(R)-2-Amino-3-phenylsulfanyl-propan-1-ol

Product 1

HCID 59323832(R)-4-Phenylsulfanylmethyl-4,5-dihydro-oxazol-2-ylamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred mixture of (R)-2-amino-3-phenylsulfanyl-propan-1-ol (0.09 g, 0.49 mmol) and K2CO3 (0.081 g, 0.59 mmol) in THF (3 ml) under an argon atmosphere was added a solution of cyanogen bromide (0.062 g, 0.59 mmol) in THF (1 ml). The mixture was stirred overnight, then ethyl acetate and water were added. The aqueous phase was back-extracted with EtOAc. The combined organics were dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: EtOAc/MeOH=95:5) to yield a light yellow solid, (0.026 g, 26%); MS (ISP): 209.1 ((M+H)+.).

Workup

  1. extractionThe aqueous phase was back-extracted with EtOAc
  2. dry with materialThe combined organics were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: EtOAc/MeOH=95:5)
  6. customto yield a light yellow solid, (0.026 g, 26%)

Sources & evidence

ORD record
ord-d9173c69c31444c49aa0270be65319d5
Source dataset
uspto-grants-2013_12
Patent number
US08604061B2

Reaction notes

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