Dicyclohexylcarbodiimide → HCID 131714247, compound

HRID 1248498Notes

Reaction equation

HRID 1248498 reaction equation
[C:1]([O:9][C@@H:10]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:11](=[O:18])[CH2:12][CH:13]([CH3:17])[C:14](O)=[O:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH:27]1[CH2:41][CH2:40][CH2:39][C@H:28]1[C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30].O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1.CCOCC>[C:1]([O:9][C@@H:10]([CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:11](=[O:18])[CH2:12][C@@H:13]([CH3:17])[C:14]([N:27]1[CH2:41][CH2:40][CH2:39][C@H:28]1[C:29]([O:31][CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)=[O:30])=[O:15])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 10868DicyclohexylcarbodiimideHCID 81531DiisopropylethylamineHCID 2733413Proline benzyl ester hydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 57247946HCID 57247946, compound

Product 1

HCID 131714247HCID 131714247, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (5S)-5-benzoyloxy-2-methyl-4-oxo-6-phenylhexanoic acid (740 mg., 2.17 mmole), L-proline, phenylmethyl ester, hydrochloride (525 mg., 2.17 mmole), 1-hydroxybenzotriazole hydrate (300 mg., 2.21 mmole), and diisopropylethylamine (0.45 ml., 2.6 mmole) in anhydrous tetrahydrofuran (8 ml.) at 0° under argon is added dropwise a solution of dicyclohexylcarbodiimide (457 mg., 2.21 mmole) in tetrahydrofuran (1.5 ml.). The resulting mixture is stirred at 0° for one hour and then warmed to room temperature. After stirring for 16 hours, the mixture is diluted with ether and washed with water, 1N hydrochloric acid (twice), 1N sodium bicarbonate, and brine. After drying (MgSO4), the solvent is removed at reduced pressure to give the desired product as a mixture of diastereomers. Flash chromatography [Whatman silica gel LPS-1; solvent, hexane:dichloromethane:ethyl acetate (6:2:2)] gives 460 mg. of 1-[(5S,2R)-5-(benzoyloxy)-2-methyl-1,4-dioxo-6-phenylhexyl]-L-proline, phenylmethyl ester; Rf =0.45 [silica gel, dichloromethane:ethyl acetate:hexane (4:3:3)].

Workup

  1. stirringAfter stirring for 16 hours
  2. washwashed with water, 1N hydrochloric acid (twice), 1N sodium bicarbonate, and brine
  3. dry with materialAfter drying (MgSO4)
  4. customthe solvent is removed at reduced pressure

Sources & evidence

ORD record
ord-0a7436fe805140baa7358ce4289a6fc0
Source dataset
uspto-grants-1985_06
Patent number
US04524212

Reaction notes

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