Hydrochloric Acid → HCID 67754521, compound

HRID 355680Notes

Reaction equation

HRID 355680 reaction equation
Cl.C(OC([NH:9][CH:10]([CH:16]([OH:30])[C:17]1[S:18][C:19]([CH2:22][CH:23]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][NH:24]2)=[CH:20][CH:21]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=O)(C)(C)C>C(O)C>[NH3:9].[NH2:9][CH:10]([CH:16]([OH:30])[C:17]1[S:18][C:19]([CH2:22][CH:23]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][NH:24]2)=[CH:20][CH:21]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67754440HCID 67754440, compound

Product 2

HCID 222AmmoniaHCID 67754521HCID 67754521, compoundYield 184.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixed solution of concentrated hydrochloric acid:ethanol=1:5 (60 ml) was added to 12.6 g of ethyl 2-tert-butoxycarbonylamino-3-hydroxy-3-[5-(1-hexahydroazepinylmethyl)-2-thienyl]propionate, and the mixture was immediately concentrated under reduced pressure, mixed with 60 ml of the above mixed solution and again concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography and elution was carried out with mixed solutions of chloroform:ethanol=60:1, chloroform:methanol=20:1 and 10:1 and chloroform:methanol:concentrated aqueous ammonia=100:10:1 in that order to obtain 8.9 g of ethyl 2-amino-3-hydroxy-3-[5-(1-hexahydroazepinylmethyl)-2-thienyl]propionate.

Workup

  1. concentrationthe mixture was immediately concentrated under reduced pressure
  2. additionmixed with 60 ml of the above mixed solution
  3. concentrationagain concentrated under reduced pressure
  4. washThe resulting residue was subjected to silica gel column chromatography and elution

Sources & evidence

ORD record
ord-11746377276243c8903e25bdfeb86b54
Source dataset
uspto-grants-1998_11
Patent number
US05834460

Reaction notes

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