Hydrochloric Acid → HCID 178477106, compound

HRID 1446804Notes

Reaction equation

HRID 1446804 reaction equation
[C:1]([S:4][CH:5]([C:21]1[N:22]=[CH:23][N:24](C(OC(C)(C)C)=O)[CH:25]=1)[CH2:6][C:7]([N:9]1[CH2:20][CH2:19][CH2:18][C@H:10]1[C:11]([O:13]C(C)(C)C)=[O:12])=[O:8])(=[O:3])[CH3:2].C1(OC)C=CC=CC=1.[ClH:41]>C(Cl)Cl>[ClH:41].[C:1]([S:4][CH:5]([C:21]1[N:22]=[CH:23][NH:24][CH:25]=1)[CH2:6][C:7]([N:9]1[CH2:20][CH2:19][CH2:18][C@H:10]1[C:11]([OH:13])=[O:12])=[O:8])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 131712665HCID 131712665, compound

Product 1

HCID 178477106HCID 178477106, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2.8 g (5.99 mmol) of (±)-1-[3-(acetylthio)-3-[1-[(1,1-dimethylethoxy)carbonyl]-1H-imidazol-4-yl]-1-oxopropyl]-L-proline, 1,1-dimethylethyl ester in 125 ml of CH2Cl2 and 6.5 ml (59.9 mmol) of anisole is cooled in an ice-water bath under nitrogen and saturated with HCl. The cold bath is removed and the stoppered flask is kept at ambient temperature for five hours. The reaction mixture is then concentrated in vacuo and the residue partitioned between 40 ml of water and 40 ml of diethyl ether. The organic solution is extracted with 20 ml more of water and the combined aqueous extracts lyophillized to afford 1.9 g of a glassy solid. This material is chromatographed on about 600 ml of LH-20 eluted with water. Pooling of the product fractions (R=0.36 on silica gel; 4:1:1:1, n-butanol:pyridine:acetic acid:water) yielded 1.9 g of product (±)-1-[3-(acetylthio)-3-(1H-imidazol-4-yl)-1-oxopropyl]-L-proline, hydrochloride.

Workup

  1. customThe cold bath is removed
  2. concentrationThe reaction mixture is then concentrated in vacuo
  3. customthe residue partitioned between 40 ml of water and 40 ml of diethyl ether
  4. extractionThe organic solution is extracted with 20 ml more of water

Sources & evidence

ORD record
ord-bf893503f948412e920e04e2bf1f7afa
Source dataset
uspto-grants-1982_02
Patent number
US04313948

Reaction notes

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