4-Methylmorpholine → Benzyl[(1S)-3-[(tert-butoxycarbonyl)amino]-1-(hydroxymethyl)propyl]carbamate

HRID 269615Notes

Reaction equation

HRID 269615 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][CH2:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:13](O)=[O:14])=[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][C@H:12]([CH2:13][OH:14])[CH2:16][CH2:17][NH:18][C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 7019789(S)-2-(((Benzyloxy)carbonyl)amino)-4-((tert-butoxycarbonyl)amino)butanoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 129308414Benzyl[(1S)-3-[(tert-butoxycarbonyl)amino]-1-(hydroxymethyl)propyl]carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Preparation takes place in analogy to Example 83A from 300 mg (0.85 mmol) of (2S)-2-{[(benzyloxy)carbonyl]amino}-4-[(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-8933c82306434e7ebac9ee6b3204b9e0
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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