Ammonia → HCID 22800292, compound

HRID 1439704Notes

Reaction equation

HRID 1439704 reaction equation
C[N:2]1[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[C:8]([O:12]N1CC(=C=O)[C@H](C)[C@H]1C(O)=O)([CH3:11])([CH3:10])[CH3:9].C(O[C:29](Cl)=[O:30])C(C)C.[NH3:32].O1[CH2:37][CH2:36]CC1>>[C:8]([O:12][C:29]([NH:32][C:6](=[O:5])[C@@H:7]1[C@@H:36]([CH3:37])[CH2:4][CH2:3][NH:2]1)=[O:30])([CH3:9])([CH3:10])[CH3:11]

Participants

6

Reactant 5

HCID 222AmmoniaHCID 79724-MethylmorpholineHCID 8028TetrahydrofuranHCID 62365Isobutyl chloroformateHCID 131710953HCID 131710953, compound

Product 1

HCID 22800292HCID 22800292, compound

Procedure

N-Methyl morpholine (6.0 ml) was added to a solution of N-t-butoxy-carbonyl-trans-3-methyl-L-proline (1.1 g) in tetrahydrofuran (50 ml) at -20°. Freshly distilled isobutylchloroformate (0.8 g) was added dropwise and the solution stirred for 10 minutes at -20°. Concentrated ammonia solution (5 ml) was added and the solution stirred for 2 hours, evaporated, the residue taken up in ethyl acetate (100 ml) and the solution washed with 10% aqueous sodium bicarbonate, brine and dried (Na2SO4). Evaporation gave the crude crystalline product (1.0 g). Recrystallisation from ethyl acetate/light petroleum (40°-60°) gave the desired product (0.91 g) m.p. 100°-101°, [α]D20 -79.7° (c, 1.0, chloroform)

Workup

  1. stirringthe solution stirred for 2 hours
  2. customevaporated
  3. washthe solution washed with 10% aqueous sodium bicarbonate, brine
  4. dry with materialdried (Na2SO4)
  5. customEvaporation

Sources & evidence

ORD record
ord-f3c4e3913de44f3bba8f2c83133a7e9c
Source dataset
uspto-grants-1977_11
Patent number
US04060603

Reaction notes

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