Hydrochloric Acid → HCID 22906456, compound

HRID 2209656Notes

Reaction equation

HRID 2209656 reaction equation
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[C:11]([O:15][CH:16]([CH3:18])[CH3:17])[CH:10]=[C:9]2[C:4]=1[C:5](=[O:27])[CH:6]=[C:7]([S:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)[O:8]2.C(OC([N:35](C(OC(C)(C)C)=O)[CH2:36][C:37](O)=[O:38])=O)(C)(C)C.C1(N=C=NC2CCCCC2)CCCCC1.[ClH:62]>ClCCl.C(OCC)(=O)C>[ClH:62].[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[C:11]([O:15][CH:16]([CH3:18])[CH3:17])[CH:10]=[C:9]2[C:4]=1[C:5](=[O:27])[CH:6]=[C:7]([S:19][C:20]1[CH:21]=[CH:22][C:23]([O:26][C:37](=[O:38])[CH2:36][NH2:35])=[CH:24][CH:25]=1)[O:8]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10868DicyclohexylcarbodiimideHCID 11509319HCID 11509319, compoundHCID 14629457N,N-Bis(tert-butoxycarbonyl)glycine

Product 1

HCID 22906456HCID 22906456, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

300 ml in dichloromethane of 9.11 g of 5,6-dimethoxy-2-(4-hydroxyphenylthio)-7-isopropoxychromone obtained in EXAMPLE 22, 4.52 g of N-t-butoxycarbonyl(Boc)glycine, and 5.32 g of dicyclohexylcarbodiimide (DCC) was stirred over 3.5 hours at room temperature. The solution thus reacted was gravitationally filtered. The solvent was distilled out from the flitrate, so that 10.95 g of N-t-butoxycarbonyl(Boc)glycine ester was obtained. 5.27 g of N-tbutoxycarbonyl(Boc)glycine ester thus prepared 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 then dried, whereby 3.53 g of 5,6-dimethoxy-2-(4-glycyloxyphenylthio)-7-isopropoxychromone 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 flitrate, so that 10.95 g of 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-36d89f8346aa45eaa19bfe2cf249196c
Source dataset
uspto-grants-1995_10
Patent number
US05455267

Reaction notes

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