Hydrochloric Acid → HCID 9887625, compound

HRID 1075693Notes

Reaction equation

HRID 1075693 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][C@@H:11]([O:15][C:16](=[O:30])[C:17]2[CH:22]=[CH:21][C:20]([O:23]C3CCCCO3)=[CH:19][CH:18]=2)[C@H:10]([NH:31][C:32](=[O:46])[C:33]2[CH:38]=[CH:37][C:36]([O:39]C3CCCCO3)=[CH:35][CH:34]=2)[CH2:9]1)=O)(C)(C)C.[ClH:47]>C(COC)OC.C(O)(C)C>[ClH:47].[OH:39][C:36]1[CH:35]=[CH:34][C:33]([C:32]([NH:31][C@H:10]2[C@H:11]([O:15][C:16](=[O:30])[C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)[CH2:12][CH2:13][CH2:14][NH:8][CH2:9]2)=[O:46])=[CH:38][CH:37]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 53968210HCID 53968210, compound

Product 1

HCID 9887625HCID 9887625, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
0 °C

Procedure

108.9 g (3R,4R)-3-[4-(Tetrahydro-pyran-2-yloxy)-benzoylamino]-4-[4-(tetrahydro-pyran-2-yloxy)-benzoyloxy]-azepane-1-carboxylic acid tert-butyl ester (mixture of 4 diast.) was dissolved in 200 ml of a 2N dimethoxyethane and i-Pr-OH (1:1) HCl solution at 0° C. The solution was kept at room temperature for 24 h. The deprotected azepine crystallized, and the reaction mixture was cooled to 0° C. before filtration. The white crystals were washed with dry ether then dissolved in pure water. The water solution was extracted twice with ether before being yand lyophilised. 66.4 g (95% yield) 4-Hydroxy-benzoic acid (3R,4R)-3-(4-hydroxy-benzoylamino)-azepan-4-yl ester hydrochloride (1:1) was obtained as a white powder

Workup

  1. customThe deprotected azepine crystallized
  2. washThe white crystals were washed with dry ether
  3. dissolutionthen dissolved in pure water
  4. extractionThe water solution was extracted twice with ether

Sources & evidence

ORD record
ord-71daaf3e8bfb46e38f5b6b20941ed5af
Source dataset
uspto-grants-1999_05
Patent number
US05907038

Reaction notes

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