4-Methylmorpholine → HCID 51340611, compound

HRID 1797267Notes

Reaction equation

HRID 1797267 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9](C)C(O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[N:15]1[CH2:20][CH2:19][O:18]CC1.[CH2:21]([O:25][C:26](Cl)=[O:27])[CH:22]([CH3:24])[CH3:23].[BH4-].[Na+].[CH2:31]1[CH2:35]OC[CH2:32]1>>[CH2:21]([O:25][C:26](=[O:27])[NH:15][C@H:20]([CH2:9][NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:19][OH:18])[C:22]1[CH:24]=[CH:35][CH:31]=[CH:32][CH:23]=1

Participants

6

Reactant 5

HCID 79724-MethylmorpholineHCID 8028Tetrahydrofuran2×HCID 62365Isobutyl chloroformateHCID 2684712-N-Boc-aminopropionic acidHCID 4311764Sodium borohydride

Product 1

HCID 51340611HCID 51340611, compound

Conditions

Temperature
0 °C

Procedure

A solution of (R)-2-benzyloxycarbonylamino-3-.tert.-butoxycarbonylamino-propionic acid (0.5 g, 1.47 mmol) in dry THF (5 ml) cooled to 0° C. is treated with N-methylmorpholine (0.16 ml, 1.47 mmol) and isobutylchloroformate (0.2 ml, 1.47 mmol). The reaction mixture is stirred at 0° C. for 15 minutes then added to a vigorously stirred suspension of sodium borohydride (0.16 g, 4.41 mmol) in dry tetrahydrofuran (5 ml) at 0° C. The reaction mixture is stirred for a further 2 hours, then quenched with water. The THF is evaporated and the remaining aqueous solution extracted into ethylacetate. The ethylacetate is washed with brine, dried over MgSO4 and evaporated to dryness. The crude product is purified by flash silica chromatography (elution with hexane:ethylacetate, 1:1) to afford [(R)-1-(tert-butoxycarbonylamino-methyl)-2-hydroxy-ethyl]-carbamic acid benzyl ester. [MH]+ 325.1

Workup

  1. stirringThe reaction mixture is stirred for a further 2 hours
  2. customquenched with water
  3. customThe THF is evaporated
  4. extractionthe remaining aqueous solution extracted into ethylacetate
  5. washThe ethylacetate is washed with brine
  6. dry with materialdried over MgSO4
  7. customevaporated to dryness
  8. customThe crude product is purified by flash silica chromatography (elution with hexane:ethylacetate, 1:1)

Sources & evidence

ORD record
ord-e1d800b62a2a49d08979e7be21bda3ff
Source dataset
uspto-grants-2006_04
Patent number
US07034042B2

Reaction notes

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