Acetic Acid → HCID 13575030, compound

HRID 279904Notes

Reaction equation

HRID 279904 reaction equation
[C:1]([CH:4]1[CH:9]([C:10]([NH:12][C@H:13]([C:15]([N:17]2[CH2:24][CH2:23][CH2:22][C@H:18]2[C:19]([OH:21])=[O:20])=[O:16])[CH3:14])=[O:11])[CH2:8][CH:7]=[CH:6][CH2:5]1)([OH:3])=[O:2].C(Cl)Cl.C(O)(=O)C>[OH-].[Na+].CO.O>[C:1]([C@@H:4]1[C@H:9]([C:10]([NH:12][C@H:13]([C:15]([N:17]2[CH2:24][CH2:23][CH2:22][C@H:18]2[C:19]([OH:21])=[O:20])=[O:16])[CH3:14])=[O:11])[CH2:8][CH:7]=[CH:6][CH2:5]1)([OH:3])=[O:2]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 6344DichloromethaneHCID 54136599HCID 54136599, compound

Product 1

HCID 13575030HCID 13575030, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent3×HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

The phenylmethyl ester product from part (a) (1.2 g., 2.31 mmole) is dissolved in a solution of 10% sodium hydroxide (5 ml.) and methanol(5 ml.) and stirred at room temperature for 3 hours. The reaction mixture is diluted with water and washed with diethyl ether. Upon acidification of the aqueous layer with potassium bisulfate and saturation with sodium chloride, the diacid product is extracted into ethyl acetate and dried (MgSO4). The ethyl acetate solution is concentrated and the residue is triturated with hexane and diethyl ether to give 400 mg. of 1-[N-[(6-carboxy-3-cyclohexen-1-yl)carbonyl]-L-alanyl]-L-proline as a white solid; m.p. softens at 98°, 125°-130°. TLC (Rf 0.44 silica gel, methylene chloride:methanol:acetic acid; 8:1:1). [α]D =-76.7° (c=1.4, methanol).

Workup

  1. washwashed with diethyl ether
  2. extractionUpon acidification of the aqueous layer with potassium bisulfate and saturation with sodium chloride, the diacid product is extracted into ethyl acetate
  3. dry with materialdried (MgSO4)
  4. concentrationThe ethyl acetate solution is concentrated
  5. customthe residue is triturated with hexane and diethyl ether
  6. customto give 400 mg
  7. customsoftens at 98°, 125°-130°

Sources & evidence

ORD record
ord-25fe585a5614418483b63123811fe4a9
Source dataset
uspto-grants-1986_05
Patent number
US04587234

Reaction notes

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