2-Amino-6-(((benzyloxy)carbonyl)amino)hexanoic acid → (S)-6-{[(Benzyloxy)carbonyl]amino}-2-bromohexanoic acid

HRID 217103노트

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HRID 217103 반응식
[Br-:1].[K+].N[CH:4]([CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C:5]([OH:7])=[O:6]>Br>[CH2:16]([O:15][C:13]([NH:12][CH2:11][CH2:10][CH2:9][CH2:8][C@H:4]([Br:1])[C:5]([OH:7])=[O:6])=[O:14])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

4

반응물 2

HCID 1025682-Amino-6-(((benzyloxy)carbonyl)amino)hexanoic acidHCID 253877Potassium Bromide

생성물 1

HCID 86762370(S)-6-{[(Benzyloxy)carbonyl]amino}-2-bromohexanoic acid

시약·촉매·용매 1

HCID 260Hydrogen Bromide용매

반응 조건

온도
0 °C

실험 절차

(S-2-Amino-6-{[(benzyloxy)carbonyl]amino}hexanoic acid, 20.0 g (0.14 mole), and potassium bromide, 28.9 g (0.24 mole), were dissolved in 80 mL of ˜6N aqueous HBr, previously chilled to 0° C. A stream of nitrogen was bubbled through the solution and the mixture was chilled to −10° C. by means of a cold bath. Sodium nitrite, 5.9 g (0.86 mole) was added in portions over 30 min with stirring, while maintaining the temperature of the reaction from −13° C. to −10° C. After 6 hours stirring at −10° C., the mixture was extracted with ethyl ether, 4×50 mL and the resulting solution dried with magnesium sulfate. The mixture was filtered to remove the drying agent and evaporated to give an orange oil. The oil was purified by flash chromatography, chloroform-hexanes to give a clear and colorless oil. The yield was 20.0 g, i.e., 81%, based on starting 2-amino-6-{[(benzyl-oxy)carbonyl]-amino}hexanoic acid. NMR is consistent with structure. (Nicolaides et al.)

후처리

  1. customA stream of nitrogen was bubbled through the solution
  2. temperaturethe mixture was chilled to −10° C. by means of a cold bath
  3. additionSodium nitrite, 5.9 g (0.86 mole) was added in portions over 30 min
  4. temperaturewhile maintaining
  5. customthe temperature of the reaction from −13° C. to −10° C
  6. stirringAfter 6 hours stirring at −10° C.
  7. extractionthe mixture was extracted with ethyl ether, 4×50 mL
  8. dry with materialthe resulting solution dried with magnesium sulfate
  9. filtrationThe mixture was filtered
  10. customto remove the drying agent
  11. customevaporated
  12. customto give an orange oil
  13. customThe oil was purified by flash chromatography, chloroform-hexanes
  14. customto give a clear and colorless oil

출처 및 근거

ORD 기록
ord-cba0db509f524eb68280df153e568b72
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193347B2

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