Triethylamine → [(4R,5R)-5-(4-methylsulfonylphenyl)-2-phenyl-4,5-dihydro-1,3-oxazol-4-yl]methanol

HRID 1879342Notes

Reaction equation

HRID 1879342 reaction equation
[NH2:1][C@H:2]([CH2:15][OH:16])[C@@H:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1)[OH:4].Cl.C(O[C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=N)C.C(N(CC)CC)C>O>[CH3:14][S:11]([C:8]1[CH:7]=[CH:6][C:5]([C@H:3]2[O:4][C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:1][C@@H:2]2[CH2:15][OH:16])=[CH:10][CH:9]=1)(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79249Benzenecarboximidic acid, ethyl ester, hydrochloride (1:1)2×HCID 6452441(R(R*,R*))-2-Amino-1-(p-(methylsulphonyl)phenyl)propane-1,3-diol2×

Product 1

HCID 14760452[(4R,5R)-5-(4-methylsulfonylphenyl)-2-phenyl-4,5-dihydro-1,3-oxazol-4-yl]methanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(1R,2R)-2-amino-1-[4-(methylsulfonyl)phenyl]-1,3-propanediol (Compound V wherein R1 is methylsulfonyl) (about 10 g, 0.04077 moles) is reacted at about 0° C. in a reaction vessel with 2,2-dichloro-ethanimidic acid ethyl ester hydrochloride (Compound IV hydrochloride wherein R2 is dichloromethyl and R4 is ethyl) (about 8.6 g, 0.0448 moles) in 1,2-dichloromethane (about 250 mL) containing triethylamine (about 4.1 g, 0.04077 moles). Next, water (about 125 mL) is added. The resulting solids are filtered, then dried to yield (4R,5R)-2-(Dichloromethyl)-4,5-dihydro-5-[4-(methylsulfonyl)phenyl]-4-oxazolemethanol (Compound II wherein R1 is methylsulfonyl and R2 is dichloromethyl).

Workup

  1. filtrationThe resulting solids are filtered
  2. customdried

Sources & evidence

ORD record
ord-1d691919eb514eac8bdc3591628443e6
Source dataset
uspto-grants-2012_11
Patent number
US08314252B2

Reaction notes

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