4-Methylmorpholine → (S)-2-Acetamido-3-(benzyloxy)propanoic acid

HRID 1764781노트

반응식

HRID 1764781 반응식
[NH2:1][C@H:2]([C:12]([OH:14])=[O:13])[CH2:3][O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:15](ON1C(=O)CCC1=O)([CH3:17])=[O:16].CN1CCOCC1>CN(C=O)C>[NH:1]([C:15]([CH3:17])=[O:16])[C@H:2]([C:12]([OH:14])=[O:13])[CH2:3][O:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

참가 물질

5

반응물 3

HCID 79724-MethylmorpholineHCID 78457O-benzyl-L-serineHCID 84460Acetic acid N-hydroxysuccinimide ester

생성물 1

HCID 10466677(S)-2-Acetamido-3-(benzyloxy)propanoic acid

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

The same compound was also prepared by a different route. Thus, H-Ser(Bzl)-OH (18.6 g, 95.4 mmol) was dissolved in 45 ml Triton B, evaporated to dryness, and the residue re-evaporated twice with DMF (100 ml each). The residue was then stirred with Ac-OSu (16.9 g, 95.4 mmol) in 150 ml DMF for 20 hours. N-Methylmorpholin was added from time to time in order to maintain the reaction slightly basic. Removal of the solvent and extraction of the product into EtOAc followed by washing with small volumes of 10% HOAc, H2O (the product is water soluble, use a small volume of H2O), dried over Na2SO4, evaporation to dryness again gave a clear oil (14.5 g, Ac-Ser(Bzl)-OH). The compound failed to crystallize. It was thus dissolved in a mixture of MeOH and H2O (300 ml:30 ml), titrated to pH 7.0 with 20% Cs2CO3 and evaporated to a solid mass. The salt was re-evaporated twice more with DMF and stirred with benzyl bromide (15.4 g, 91 mmol) in 250 ml DMF for 18 hours. On evaporation of the solvent, the residue was taken up in H2O (600 ml) and the oily product formed was extracted into EtOAc. It was washed with H2O, dried over Na2SO4 and evaporated to a syrup which on seeding crystallized immediately. It was recrystallized from EtOAc and petroleum ether to yield, 10.42 g (32.2% overall); mp 89°-91°.

후처리

  1. customThe same compound was also prepared by a different route
  2. customevaporated to dryness
  3. customthe residue re-evaporated twice with DMF (100 ml each)
  4. temperatureto maintain
  5. customthe reaction slightly basic
  6. customRemoval of the solvent and extraction of the product into EtOAc
  7. washby washing with small volumes of 10% HOAc, H2O (the product
  8. dry with materialdried over Na2SO4, evaporation to dryness

출처 및 근거

ORD 기록
ord-52d30531508945e1af648a34b9848be1
출처 데이터셋
uspto-grants-1978_09
특허 번호
US04116951

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