HCID 15523989, compound → HCID 11123362, compound

HRID 1978208Notes

Reaction equation

HRID 1978208 reaction equation
C([S:4][CH2:5][CH2:6][C@@H:7]([C:19]([NH:21][C@H:22]([C:32]([O:34][CH3:35])=[O:33])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH:30]=[O:31])=[O:20])[NH:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])(=O)C>CO.C(Cl)Cl>[CH:30]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[CH2:23][C@@H:22]([C:32]([O:34][CH3:35])=[O:33])[NH:21][C:19](=[O:20])[C@H:7]([CH2:6][CH2:5][SH:4])[NH:8][C:9]([O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:10])=[O:31]

Participants

4

Reactant 1

HCID 15523989HCID 15523989, compound

Product 1

HCID 11123362HCID 11123362, compoundYield 104.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of the title compound of step (J) (0.77 g, 1.54 mmol) in MeOH (16 mL) and CH2Cl2 (3 mL) cooled at 0° C. was purged with argon for 20 minutes. To this solution 370 μL of NaOMe (25% w/w in MeOH) was added dropwise. After addition, the mixture was stirred at 0° C. for 15 minutes before being quenched with sat. aqueous NH4Cl (20 mL). The mixture was extracted with EtOAc (200 mL). The separated aqueous phase was back-extracted with EtOAc (50 mL). The combined EtOAc was washed with sat. aqueous NH4Cl, H2O, brine, dried (MgSO4), filtered, concentrated and dried in vacuo to give 0.736 g of the title compound of this step as a white foam which was used in the next reaction step without further purification.

Workup

  1. customwas purged with argon for 20 minutes
  2. additionTo this solution 370 μL of NaOMe (25% w/w in MeOH) was added dropwise
  3. additionAfter addition
  4. custombefore being quenched with sat. aqueous NH4Cl (20 mL)
  5. extractionThe mixture was extracted with EtOAc (200 mL)
  6. extractionThe separated aqueous phase was back-extracted with EtOAc (50 mL)
  7. washThe combined EtOAc was washed with sat. aqueous NH4Cl, H2O, brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customdried in vacuo

Sources & evidence

ORD record
ord-bf6bf54bb76a4253b51e77e104200bbb
Source dataset
uspto-grants-2001_05
Patent number
US06235922B1

Reaction notes

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