Morpholine → HCID 69707996, compound

HRID 2414375Notes

Reaction equation

HRID 2414375 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([O:23]CC=C)=[O:22])[CH:16]=1)[C:10]#[N:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1CCOCC1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([OH:23])=[O:22])[CH:16]=1)[C:10]#[N:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 8083MorpholineHCID 69706963HCID 69706963, compound

Product 1

HCID 69707996HCID 69707996, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-2-t-butoxycarbonylamino-3-(3-allyloxycarbonylbenzyloxy)-propionitrile (8.0 g, 22.22 mmol) in THF (100 mL) is added morpholine (19.4 mL, 222 mmol). After deoxygenation with bubbling nitrogen (2 min.), Pd(PPh3)4 (1.28 g, 1.11 mmol) is added in one portion, and the solution is stirred 1 h. Solvent is evaporated, the residue is taken up in EtOAc (250 mL), and washed with 1 N HCl (250 mL), brine (100 mL), dried (MgSO4), evaporated, and the residue chromatographed (silica, 2% methanol, CH2Cl2) to yield (S)-2-t-butoxycarbonylamino-3-(3-carboxybenzyloxy)-propionitrile, as a light yellow oil.

Workup

  1. customSolvent is evaporated
  2. washwashed with 1 N HCl (250 mL), brine (100 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customthe residue chromatographed (silica, 2% methanol, CH2Cl2)

Sources & evidence

ORD record
ord-13a69d781a4e4aad92b104f25654c1db
Source dataset
uspto-grants-2004_11
Patent number
US06812237B2

Reaction notes

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