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4-Methylmorpholine → [(R)-3-diazo-1-(4-methoxy-benzylsulfanylmethyl)-2-oxo-propyl]-carbamic acid t-butyl ester

HRID 336445
Notes
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Reaction equation

HRID 336445 reaction equation
C([C@@:8]([NH2:23])([CH2:12][S:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[C:9]([OH:11])=O)(OC(C)(C)C)=O.[CH3:24]N1CCOCC1.C(O[C:34](Cl)=[O:35])C.[OH-:37].[K+].[CH3:39][N:40]([N:44]=O)C(N)=O.O1[CH2:50][CH2:49][CH2:48]C1>O.C(OCC)C>[C:49]([O:37][C:34](=[O:35])[NH:23][C@@H:8]([CH2:12][S:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1)[C:9](=[O:11])[CH:39]=[N+:40]=[N-:44])([CH3:48])([CH3:50])[CH3:24]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 6

HCID 79724-MethylmorpholineHCID 8028TetrahydrofuranHCID 10928Ethyl chloroformateHCID 12699N-Methyl-N-nitrosoureaHCID 14797Potassium HydroxideHCID 68486000(R)-2-BOC-amino-3-(4-methoxy-benzylsulfanyl)-propionic acid

Product 1

HCID 86672690
[(R)-3-diazo-1-(4-methoxy-benzylsulfanylmethyl)-2-oxo-propyl]-carbamic acid t-butyl ester
Yield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-25 °C

Procedure

(R)-2-BOC-amino-3-(4-methoxy-benzylsulfanyl)-propionic acid (43 g, 132 mmol) prepared in Step B, 1-methylmorpholine (14.5 mL, 132 mmol) and ethylchloroformate (14.1 mL, 132 mmol) were dissolved in tetrahydrofuran (500 mL), and the mixture was stirred for 1 h at −25° C. At the same time, potassium hydroxide (75 g, 1336 mmol) was dissolved in water (75 mL) and diethylether (750 mL), N-methyl-nitrosourea (26 g, 252 mmol) was added in drops thereto over 2 h at 0° C., and the mixture was stirred for 30 min. The two solutions thus obtained were mixed together, and stirred for 3 h at −25° C. to room temperature. After completion of the reaction, water was added to the reaction mixture, which was then washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous ammonium chloride solution in the order. The organic layer was concentrated to give the title compound (46.0 g, Yield 95%).

Workup

  1. waitover 2 h at 0° C.
  2. stirringthe mixture was stirred for 30 min
  3. customThe two solutions thus obtained
  4. additionwere mixed together
  5. stirringstirred for 3 h at −25° C. to room temperature
  6. additionwas added to the reaction mixture, which
  7. washwas then washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous ammonium chloride solution in the order
  8. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-81b1320c0299424cbca1f3cbf17faa69
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08889691B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes