Morpholine → HCID 53709844, compound

HRID 1655748Notes

Reaction equation

HRID 1655748 reaction equation
[CH2:1]([O:3][C:4]([CH:6]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:7][CH2:8][C:9]([OH:11])=O)=[O:5])[CH3:2].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[NH:55]1[CH2:60][CH2:59][O:58][CH2:57][CH2:56]1>C(#N)C.C(Cl)(Cl)Cl.CO>[CH2:1]([O:3][C:4](=[O:5])[CH:6]([CH2:7][CH2:8][C:9]([N:55]1[CH2:60][CH2:59][O:58][CH2:57][CH2:56]1)=[O:11])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:2]

Participants

8

Reactant 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 19790946HCID 19790946, compound

Product 1

HCID 53709844HCID 53709844, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

600 mg (2.4 mmol) of (RS)-4-(ethoxycarbonyl)-5-phenylvaleric acid in 20 ml of acetonitrile were treated with 1.06 g (2.4 mmol) of BOP, 310 mg of Hunig base and 0.21 ml of morpholine and stirred at room temperature for 1 hour and thereafter at 50° for 2 hours. After the usual working-up and chromatography on silica gel using a 10:1 mixture of methanol and chloroform as the eluting agent, there were obtained 400 mg (52%) of (RS)-α-[2-(morpholinocarbonyl)ethyl]hydrocinnamic acid ethyl ester which was used directly in the next step. MS: 319 (M+).

Workup

  1. waitat 50° for 2 hours

Sources & evidence

ORD record
ord-497e5df2ce7b411e8407b7a874037480
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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