Hydrochloric Acid → HCID 86754076, compound

HRID 369450Notes

Reaction equation

HRID 369450 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][C@@H:11]([O:15][C:16](=[O:24])[C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[C@H:10]([NH:25][C:26](=[O:43])[C:27]2[CH:32]=[CH:31][C:30]([O:33][C:34](=[O:42])[C:35]3[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=3)=[CH:29][CH:28]=2)[CH2:9]1)=O)(C)(C)C.[ClH:44]>C(COC)OC.C(O)(C)C>[ClH:44].[F:41][C:38]1[CH:37]=[CH:36][C:35]([C:34]([O:33][C:30]2[CH:31]=[CH:32][C:27]([C:26]([NH:25][C@H:10]3[C@H:11]([O:15][C:16](=[O:24])[C:17]4[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=4)[CH2:12][CH2:13][CH2:14][NH:8][CH2:9]3)=[O:43])=[CH:28][CH:29]=2)=[O:42])=[CH:40][CH:39]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 53976939HCID 53976939, compound

Product 1

HCID 86754076HCID 86754076, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
0 °C

Procedure

56 mg (3R,4R)-3-[4-(4-Fluoro-benzoyloxy)-benzoylamino]-4-(4-hydroxy-benzoyloxy)-azepane-1-carboxylic acid tert-butyl ester was dissolved in 2 ml dimethoxyethane and 2 ml isopropanol (i-Pr-OH); after cooling to 0° C. the solution was slowly saturated with HCl-gas and stored in a refrigerator for 24 h. The solvent was completely removed in vacuo; the product was triturated with diethylether; the resulting suspension was stirred for several hours. The solvent was decanted and stirring was continued overnight after addition of another portion of fresh solvent. The product was filtered, washed with several portions of diethylether and dried in vacuo (0.1 mbar) at 50° C. 40 mg (85% yield) 4-Hydroxy-benzoic acid (3R,4R)-3-[4-(4-fluoro-benzoyloxy)-benzoylamino]-azepan-4-yl ester hydrochloride (1:1) was obtained as a yellow powder

Workup

  1. customThe solvent was completely removed in vacuo
  2. customthe product was triturated with diethylether
  3. customThe solvent was decanted
  4. stirringstirring
  5. waitwas continued overnight
  6. additionafter addition of another portion of fresh solvent
  7. filtrationThe product was filtered
  8. washwashed with several portions of diethylether
  9. customdried in vacuo (0.1 mbar) at 50° C

Sources & evidence

ORD record
ord-b018f622a70147f4b50b3159557004a5
Source dataset
uspto-grants-2000_10
Patent number
US06136969

Reaction notes

Loading…