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Water → HCID 68464125, compound

HRID 507439
Notes
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Reaction equation

HRID 507439 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][C:8]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:12][CH:11](O)[O:10][C:9]1=[O:14])([CH3:4])([CH3:3])[CH3:2].C([O-])(O)=O.[Na+].[NH2:27][C@H:28]([C:31]([O:33][CH3:34])=[O:32])[CH2:29][SH:30].Cl.O>CCO>[CH3:34][O:33][C:31]([CH:28]1[CH2:29][S:30][CH:11]([CH2:12][C:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:21])([C:9]([OH:10])=[O:14])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[NH:27]1)=[O:32]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium Bicarbonate2×HCID 2733208L-Cysteine, methyl ester, hydrochlorideHCID 57443730HCID 57443730, compound

Product 1

HCID 68464125HCID 68464125, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Procedure

To a solution of compound 14 (5.6 g, 19.1 mmol) in EtOH (80 mL) was added 1 M aq. NaHCO3 solution (19.1 mL, 19.1 mmol), followed by the addition of L-Cys-OMe.HCl (3.3 g 19.1 mmol). The pH value of the resulting mixture was adjusted to 6.5 with 1 M NaHCO3 solution. After stirring overnight, the mixture was poured into water, extracted with ethyl acetate, and the combined organic phases were dried over Na2SO4 and concentrated to afford product 15 (7 g, 51.1%). MS (M+1): 411. This product was used in the next step without further purification.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialthe combined organic phases were dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6e83a83ff7154910be03c248d4b5a38a
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07786163B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes