Hydrochloric Acid → HCID 15230866, compound

HRID 1464515Notes

Reaction equation

HRID 1464515 reaction equation
[CH3:1][C:2]1[C:7](=[O:8])[C:6]([CH3:9])=[C:5]([CH3:10])[C:4](=[O:11])[C:3]=1[CH:12]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](NCC(OCC1C=CC=CC=1)=O)=[O:19].[NH:38]1[CH2:45][CH2:44][CH2:43][C@H:39]1[C:40]([OH:42])=[O:41].C(N1CCOCC1)C.Cl>CN(C)C=O>[CH3:1][C:2]1[C:7](=[O:8])[C:6]([CH3:9])=[C:5]([CH3:10])[C:4](=[O:11])[C:3]=1[CH:12]([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([N:38]1[CH2:45][CH2:44][CH2:43][C@H:39]1[C:40]([OH:42])=[O:41])=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7525EthylmorpholineHCID 145742L-ProlineHCID 19088032HCID 19088032, compound

Product 1

HCID 15230866HCID 15230866, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of benzyl 7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-7-phenylheptanoylglycinate (0.95, 2.0 mmoles) and L-proline (0.24 g, 2.1 mmoles) was added a solution of N-ethylmorpholine (0.48 g, 4.2 mmoles), in dimethylformamide (10 ml) at room temperature. After 15 hours, 1N hydrochloric acid (5 ml) was added to the reaction mixture. The product was extracted with ethylacetate. The extract was worked up in the usual manner. The crude product was chromatographed on a reversed phase ODS column (YMC-Gel ODS, 60/200 mesh, Yamamura Chemical Co. Kyoto) with methanol-H2O (9:1) as eluant to give 7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-7-phenylheptanoyl-L-proline (0.64 g, 71%) as an oil.

Workup

  1. customat room temperature
  2. extractionThe product was extracted with ethylacetate
  3. customThe crude product was chromatographed on a reversed phase ODS column (YMC-Gel ODS, 60/200 mesh, Yamamura Chemical Co. Kyoto) with methanol-H2O (9:1) as eluant

Sources & evidence

ORD record
ord-4199e0b12abe40fcba5000c246ce75fa
Source dataset
uspto-grants-1994_04
Patent number
US05304658

Reaction notes

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