Hydrochloric Acid → HCID 22906532, compound

HRID 1779517Notes

Reaction equation

HRID 1779517 reaction equation
[CH2:1]([O:3][C:4]1[C:13]([O:14][CH3:15])=[C:12]([O:16][CH:17]([CH3:19])[CH3:18])[CH:11]=[C:10]2[C:5]=1[C:6](=[O:28])[CH:7]=[C:8]([S:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1)[O:9]2)[CH3:2].C(OC([N:36](C(OC(C)(C)C)=O)[CH2:37][C:38](O)=[O:39])=O)(C)(C)C.C1(N=C=NC2CCCCC2)CCCCC1.[ClH:63]>ClCCl.C(OCC)(=O)C>[ClH:63].[CH2:1]([O:3][C:4]1[C:13]([O:14][CH3:15])=[C:12]([O:16][CH:17]([CH3:19])[CH3:18])[CH:11]=[C:10]2[C:5]=1[C:6](=[O:28])[CH:7]=[C:8]([S:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:38](=[O:39])[CH2:37][NH2:36])=[CH:23][CH:22]=1)[O:9]2)[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10868DicyclohexylcarbodiimideHCID 14629457N,N-Bis(tert-butoxycarbonyl)glycineHCID 15288794HCID 15288794, compound

Product 1

HCID 22906532HCID 22906532, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

300 ml in dichloromethane of 11.35 g of 5-ethoxy-2-(4-hydroxyphenylthio)-7-isopropoxy-6-methoxychromone obtained in Example 18, 5.43 g of N-t-butoxycarbonyl(Boc)glycine, and 6.40 g of dicyclohexylcarbodiimide (DCC) was stirred over 5.5 hours at room temperature. The solution thus reacted was gravitationally filtered. The solvent was distilled out from the filtrate, so that N-t-butoxycarbonyl(Boc)glycine ester was obtained. This product was dissolved in 100 ml of ethyl acetate. Then, hydrochloric acid gas was introduced and bubbled in the solution for 10 min., followed by stirring for 1 hour. Subsequently, 200 ml ether was added and the resulting crystals were collected by filtration and dried, whereby 11.28 g of 5-ethoxy-2-(4-glycyloxyphenylthio)-7-isopropoxy-6-methoxychromone hydrochloride with the following physicochemical properties was obtained.

Workup

  1. customThe solution thus reacted
  2. filtrationwas gravitationally filtered
  3. distillationThe solvent was distilled out from the filtrate, so that N-t-butoxycarbonyl(Boc)glycine ester
  4. customwas obtained
  5. custombubbled in the solution for 10 min.
  6. additionSubsequently, 200 ml ether was added
  7. filtrationthe resulting crystals were collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-d2cf80125ab54c0dad2bb22187cead02
Source dataset
uspto-grants-1997_05
Patent number
US05627204

Reaction notes

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