4-Methylmorpholine → Tert-butoxycarbonylalanine

HRID 615338Notes

Reaction equation

HRID 615338 reaction equation
[NH:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:2]([C:4]([OH:6])=[O:5])[CH3:3].C[N:15]1[CH2:20][CH2:19]O[CH2:17][CH2:16]1.Cl[C:22]([O:24][CH2:25][CH:26]([CH3:28])[CH3:27])=[O:23].O1C[CH2:32][CH2:31][CH2:30]1>C(Cl)(Cl)Cl>[NH:1]([C:7]([O:9][C:10]([CH3:11])([CH3:13])[CH3:12])=[O:8])[C@H:2]([C:4]([OH:6])=[O:5])[CH3:3].[NH:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:2]([C:4]([N:15]1[CH2:16][CH2:17][CH2:19][C@H:20]1[C:22]([O:24][CH2:25][C:26]1[CH:28]=[CH:32][CH:31]=[CH:30][CH:27]=1)=[O:23])=[O:6])[CH3:3]

Participants

7

Reactant 4

HCID 79724-Methylmorpholine2×HCID 8028TetrahydrofuranHCID 62365Isobutyl chloroformateHCID 85082Tert-butoxycarbonylalanine

Product 2

HCID 85082Tert-butoxycarbonylalanineHCID 13068139N-[(1,1-Dimethylethoxy)carbonyl]-L-alanyl-L-proline phenylmethyl ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixed anhydride of Boc-Ala-OH was prepared by reacting Boc-Ala-OH (10 g, 52.8 mmoles) with N-methylmorpholine (5.80 mL, 52.8 mmoles) and isobutyl chloroformate (6.8 mL, 52.85 mmoles) for 5 minutes in 50 mL of tetrahydrofuran at -20°. The reaction mixture and additional N-methylmorpholine (5.8 mL) were added to H-Pro-Obzl·HCl dissolved in 50 mL of cold CHCl3. After this mixture was stirred for 1 hour at -20° and 2 hours at 23°, it was filtered and the filtrate evaporated. The residue was dissolved in ethyl acetate and was washed sequentially with 0.2N HCl, 5% NaHCO3, and saturated aqueous NaCl. The solvent was evaporated to yield Boc-AlaPro-OBzl as an oil (14.1 g).

Workup

  1. customfor 5 minutes
  2. customat -20°
  3. filtrationit was filtered
  4. customthe filtrate evaporated
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwas washed sequentially with 0.2N HCl, 5% NaHCO3, and saturated aqueous NaCl
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-74c571b1595845399a62deb51f50d13a
Source dataset
uspto-grants-1985_02
Patent number
US04499082

Reaction notes

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