4-Methylmorpholine → Benzyl (2R)-2-Benzyl-3-thiazol-4-ylpropionate

HRID 973501Notes

Reaction equation

HRID 973501 reaction equation
[CH2:1]([C@H:8]([CH2:19][C:20]([CH2:22]Cl)=O)[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:24]([NH2:26])=[S:25].CN1CCOCC1>CC(C)=O.CCOCC>[CH2:1]([C@H:8]([CH2:19][C:20]1[N:26]=[CH:24][S:25][CH:22]=1)[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 79724-MethylmorpholineHCID 3005587MethanethioamideHCID 10449338Benzyl (2R)-2-Benzyl-3-chloromethylcarbonylpropionate

Product 1

HCID 15018104Benzyl (2R)-2-Benzyl-3-thiazol-4-ylpropionateYield 76%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

The resultant compound from Example 34 (476.8 mg, 1.44 mmol) and thioformamide (176 mg, 2.88 mmol) in acetone (6 ml) were stirred at room temperature for 108 h. N-methylmorpholine (0.16 ml, 1.40 mmol) was added and after 20 min the mixture was diluted with ether, filtered, evaporated, and chromatographed on silica gel with 20% ethyl acetate in hexane to afford 369 mg (76%) of an oil. 1H NMR (CDCl3) δ8.70 (d,1H), 7.05-7.35 (m,10H), 6.90 (d,1H), 5.00 (d,1H), 4.95 (d,1H), 3.28-3.35 (m,1H), 3.19 (dd,1H), 2.95-3.10 (m,2H), 2.88 (dd,1H).

Workup

  1. filtrationfiltered
  2. customevaporated
  3. customchromatographed on silica gel with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-811b13b68f8144ab849148ce71fd67f0
Source dataset
uspto-grants-1991_11
Patent number
US05063208

Reaction notes

Loading…