Hydrochloric Acid → HCID 86750059, compound

HRID 1290134Notes

Reaction equation

HRID 1290134 reaction equation
[F:1][C:2]1[C:45]([O:46][CH3:47])=[CH:44][CH:43]=[C:42]([O:48]COC)[C:3]=1[C:4]([C:6]1[CH:41]=[CH:40][C:9]([C:10]([O:12][C@@H:13]2[CH2:19][CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][C@H:14]2[NH:27][C:28](=[O:39])[C:29]2[CH:34]=[CH:33][C:32]([O:35]COC)=[CH:31][CH:30]=2)=[O:11])=[CH:8][CH:7]=1)=[O:5].C(O)(C)C.[ClH:56]>C(COC)OC>[ClH:56].[OH:35][C:32]1[CH:31]=[CH:30][C:29]([C:28]([NH:27][C@H:14]2[C@H:13]([O:12][C:10](=[O:11])[C:9]3[CH:8]=[CH:7][C:6]([C:4](=[O:5])[C:3]4[C:42]([OH:48])=[CH:43][CH:44]=[C:45]([O:46][CH3:47])[C:2]=4[F:1])=[CH:41][CH:40]=3)[CH2:19][CH2:18][CH2:17][NH:16][CH2:15]2)=[O:39])=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 54137644HCID 54137644, compound

Product 1

HCID 86750059HCID 86750059, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

639.7 mg of tert-butyl (3R,4R)-4-[4-(2-fluoro-3-methoxy-6-methoxymethoxy-benzoyl)-benzoyloxy]-3-(4-methoxymethoxy-benzoylamino)-azepane-1-carboxylate were dissolved in 9 ml of dimethoxyethane and 9 ml of isopropanol and, after cooling to 0° C., saturated slowly with HCl gas and stored in a refrigerator for 24 hours. The solvent was removed completely under reduced pressure and the product was triturated with diethyl ether. The suspension obtained was stirred for several hours; the solvent was decanted off and, after the addition of a further amount of fresh solvent, the stirring was continued overnight. The product was filtered off, washed several times with diethyl ether and dried at 0.1 mbar and 50° C. There were obtained 479 mg of 4-(2-fluoro-6-hydroxy-3-methoxy-benzoyl)-benzoic acid (3R,4R)-3-(4-hydroxy-benzoylamino)-azepan-4-yl ester hydrochloride (1:1) as a yellow powder.

Workup

  1. customThe solvent was removed completely under reduced pressure
  2. customthe product was triturated with diethyl ether
  3. customThe suspension obtained
  4. customthe solvent was decanted off
  5. additionafter the addition of a further amount of fresh solvent
  6. waitthe stirring was continued overnight
  7. filtrationThe product was filtered off
  8. washwashed several times with diethyl ether
  9. customdried at 0.1 mbar and 50° C

Sources & evidence

ORD record
ord-98184803a3464864bac47166f6e23a83
Source dataset
uspto-grants-1998_05
Patent number
US05750706

Reaction notes

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