4-Methylmorpholine → Boc-Dab(Z)-Ol (S)

HRID 269670Notes

Reaction equation

HRID 269670 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][C@H:14]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:15](O)=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1CCOCC1.ClC(OCC)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:1]([O:8][C:9](=[O:10])[NH:11][CH2:12][CH2:13][C@H:14]([NH:18][C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[CH2:15][OH:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 7019688(S)-4-(((Benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)butanoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 59722512Boc-Dab(Z)-Ol (S)

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Preparation takes place in analogy to Example 83A from 300 mg (0.85 mmol) of (2S)-4-{[(benzyloxy)carbonyl]amino}-2-[(tert-butoxycarbonyl)amino]butanoic acid in 10 ml of tetrahydrofuran with 86 mg (0.85 mmol) of 4-methylmorpholine, 92 mg (0.85 mmol) of ethyl chloroformate and 1.7 ml (1.70 mmol) of a 1M solution of lithium aluminum hydride in tetrahydrofuran. The product is reacted without further purification.

Workup

  1. customPreparation
  2. customThe product is reacted without further purification

Sources & evidence

ORD record
ord-60604a3067644fe79d6e7bf71d83fd31
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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