Triethylamine → HCID 86605382, 화합물

HRID 1180442노트

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HRID 1180442 반응식
[C:1]([OH:9])(=O)[C@H:2]([CH2:4][CH:5]([CH3:7])[CH3:6])[OH:3].Cl.[NH2:11][CH2:12][C:13]#[N:14].C(N(CC)CC)C.C([O-])(O)=O.[Na+]>CN(C=O)C.CCOC(C)=O.CCCCCC>[C:12]([CH2:13][NH:14][C:1](=[O:9])[C@@H:2]([OH:3])[CH2:4][CH:5]([CH3:6])[CH3:7])#[N:11]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 83697Leucic acid, L-HCID 516892Sodium BicarbonateHCID 11491918Aminoacetonitrile hydrochloride

생성물 1

HCID 86605382HCID 86605382, 화합물

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 21226206Ethyl acetate hexane용매

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온도
0 °C

실험 절차

L-leucic acid (85 g, 0.643 mole), amino acetonitrile hydrochloride (68 g, 0.734 mole, 1.14 eg), pyBOP (319 g, 0.612 mole, 0.95 eg) were mixed together in DMF (1 L) and cooled at 0° C. Triethylamine (149 g, 1.47 mole, 2.4 eg) was added dropwise at a rate to maintain internal temperature ≦20° C. Reaction mixture was then allowed to warm to room temperature and stirred for 18 hours. Reaction mixture was poured portionwise into saturated NaHCO3 (4 L) and extracted with EtOAc (2×1 L). Half saturated NaCl solution was added to help partition. Combined organic fractions were washed with brine, 0.5 N HCl, brine, dried and evaporated to give a dark red oil. The latter was passed through a silica plug with 50% EtOAc/hexane to give of the title compound.

후처리

  1. temperatureto maintain internal temperature ≦20° C
  2. customReaction mixture
  3. temperatureto warm to room temperature
  4. customReaction mixture
  5. extractionextracted with EtOAc (2×1 L)
  6. additionHalf saturated NaCl solution was added
  7. customto help partition
  8. washCombined organic fractions were washed with brine, 0.5 N HCl, brine
  9. customdried
  10. customevaporated
  11. customto give a dark red oil

출처 및 근거

ORD 기록
ord-45c0a8ce5ce0442d91c2be7ad1a2d3cb
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07279478B2

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