Morpholine → HCID 10989798, compound

HRID 1646533Notes

Reaction equation

HRID 1646533 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:10]Br)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[NH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>C1COCC1>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:10][N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 18649580HCID 18649580, compound

Product 1

HCID 10989798HCID 10989798, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of N-tert-butoxycarbonyl-1-bromo-2-(S)-amino-4-methylpentane 1.76 g, 6.3 mmol) and triethylamine (0.96 ml, 6.9 mmol) in THF (50 ml) at room temperature was added morpholine (0.60 ml, 6.9 mmol). The mixture was stirred overnight and the solvent removed under reduced pressure. The residue was partitioned between saturated aqueous ammonium chloride (50 ml) and ethyl acetate (2×100 ml). The crude N-tert-butoxycarbonyl-1-morpholino-2-(S)-amino-4-methylpentane was then used directly in the next step.

Workup

  1. customthe solvent removed under reduced pressure
  2. customThe residue was partitioned between saturated aqueous ammonium chloride (50 ml) and ethyl acetate (2×100 ml)

Sources & evidence

ORD record
ord-df22b4538593456195b1b38b069ae804
Source dataset
uspto-grants-1993_01
Patent number
US05180723

Reaction notes

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