Ethylmorpholine → HCID 70519969, compound

HRID 544264Notes

Reaction equation

HRID 544264 reaction equation
Cl.[CH2:2]([O:9][C:10](=[O:16])[C@@H:11]1[CH2:15][CH2:14][CH2:13][NH:12]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:17]12(CC(O)=O)[CH2:26][CH:21]3[CH2:22][CH:23]([CH2:25][CH:19]([CH2:20]3)[CH2:18]1)[CH2:24]2.ON1C2C=CC=CC=2N=N1.C(N1CC[O:46][CH2:45][CH2:44]1)C.C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C.CN(C)C=O>[CH2:2]([O:9][C:10](=[O:16])[C@:11]1([C:45](=[O:46])[CH3:44])[CH2:15][CH2:14][CH2:13][N:12]1[C:17]12[CH2:26][CH:21]3[CH2:20][CH:19]([CH2:25][CH:23]([CH2:22]3)[CH2:24]1)[CH2:18]2)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

8

Reactant 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 1232211-Adamantaneacetic acidHCID 2733413Proline benzyl ester hydrochloride

Product 1

HCID 70519969HCID 70519969, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4.8 g (0.02 m) of L-proline benzyl ester hydrochloride, 3.88 g (0.02 m) of α-(1-adamantyl)acetic acid, 5.4 g (0.04 m) of 1-hydroxybenzotriazole, 2.56 ml of N-ethylmorpholine, 60 ml of dimethylformamide and 4.16 g (0.02 m) of dicyclohexylcarbodiimide was stirred overnight at 25°. The mixture was filtered and the tetrahydrofuran removed in vacuo from the filtrate to leave a residue which was taken up in 200 ml of ethyl acetate. The resulting extract was acidified with dilute hydrochloride acid. The layers were separated. The organic layer was extracted several times with ethyl acetate. The organic extracts were combined and washed with dilute acid, water, bicarbonate solution and brine then dried and evaporated to give an amber syrup of N-(1-adamantyl)-ethanoylproline benzyl ester, m/e=381. A second run on a 0.04 m scale gave 16.2 g of ester.

Workup

  1. filtrationThe mixture was filtered
  2. customthe tetrahydrofuran removed in vacuo from the filtrate
  3. customto leave a residue which
  4. extractionThe resulting extract
  5. customThe layers were separated
  6. extractionThe organic layer was extracted several times with ethyl acetate
  7. washwashed
  8. additionwith dilute acid, water, bicarbonate solution and brine
  9. customthen dried
  10. customevaporated

Sources & evidence

ORD record
ord-fde631c0bc3e4dd7a4987c5a0484bb0f
Source dataset
uspto-grants-1984_05
Patent number
US04448972

Reaction notes

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