Hydrochloric Acid → (R)-Fmoc-isoserine

HRID 412419

반응식

HRID 412419 반응식
CC1(C)[O:6][C@H:5]([CH2:7]C(O)=O)[C:4](=[O:11])[O:3]1.C([N:15]([CH2:18]C)CC)C.[O:20](P(N=[N+]=[N-])(OC1C=CC=CC=1)=O)C1C=CC=CC=1.[CH:39]1[C:51]2[CH:50]([CH2:52][OH:53])[C:49]3[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=3)[C:43]=2[CH:42]=[CH:41][CH:40]=1.Cl>C(#N)C.C1(C)C=CC=CC=1>[C:18]([NH:15][CH2:7][C@H:5]([C:4]([OH:3])=[O:11])[OH:6])([O:53][CH2:52][CH:50]1[C:51]2[C:43](=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:44]2[C:49]1=[CH:48][CH:47]=[CH:46][CH:45]=2)=[O:20]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 904669H-Fluorene-9-methanolHCID 123414Diphenylphosphoryl azideHCID 108449602-((4R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)acetic acid

생성물 1

HCID 7408673(R)-Fmoc-isoserine수율 36.4%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6342Acetonitrile용매

반응 조건

온도
100 °C

실험 절차

To (R)-(2,2-dimethyl-5-oxo[1,3]dioxolan-4-yl)acetic acid (5.88 g, 33.8 mmol) was added toluene (100 mL), triethylamine (4.7 mL, 33.8 mmol) and diphenoxyphosphoryl azide (8.0 mL, 37.2 mmol). The reaction mixture was heated to a 100° C and stirred under nitrogen at this temperature for 1.5 hour. 9-Fluorenemethanol (5.1 g, 26 mmol) was added and the reaction mixture was refluxed for 6 hours. After cooling to room temperature the mixture was transferred to a separatory funnel and washed with water (2×50 mL). The solvent was removed in vacuo and co-evaporated with acetonitrile (100 mL). The remaining light brown oil was dissolved in DCM (20 mL) and purified on silica gel column with DCM as eluent. The DCM was removed by evaporation to yield a light yellow oil, which was redissolved in acetonitrile (150 mL) and aqueous hydrochloric acid was added (1 N, 75 mL). The yellow reaction mixture was stirred for 3 hours at room temperature. The solvent was removed in vacuo, toluene (100 mL) was added and the suspension was heated to reflux and allowed to cool to room temperature. (R)-Fmoc-isoserine (3.1 g, 28%) was isolated as a powder by filtration. Mp: 165-166° C.

후처리

  1. temperaturethe reaction mixture was refluxed for 6 hours
  2. temperatureAfter cooling to room temperature the mixture
  3. customwas transferred to a separatory funnel
  4. washwashed with water (2×50 mL)
  5. customThe solvent was removed in vacuo and co-evaporated with acetonitrile (100 mL)
  6. dissolutionThe remaining light brown oil was dissolved in DCM (20 mL)
  7. custompurified on silica gel column with DCM as eluent
  8. customThe DCM was removed by evaporation
  9. customto yield a light yellow oil, which
  10. stirringThe yellow reaction mixture was stirred for 3 hours at room temperature
  11. customThe solvent was removed in vacuo, toluene (100 mL)
  12. additionwas added
  13. temperaturethe suspension was heated
  14. temperatureto reflux
  15. temperatureto cool to room temperature

출처 및 근거

ORD 기록
ord-edb909f74e214773a415ea5dd300654e
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06562807B2

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