Triethylamine → HCID 178501427, 화합물

HRID 1197925노트

반응식

HRID 1197925 반응식
[C:1]([CH2:7][C@@H:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:9]([OH:11])=O)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].Cl.Cl.[CH3:21][O:22][C:23](=[O:32])[C@H:24]([CH2:26][C:27]1[N:31]=[CH:30][NH:29][CH:28]=1)[NH2:25].C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O>[CH3:21][O:22][C:23](=[O:32])[C@H:24]([CH2:26][C:27]1[N:31]=[CH:30][NH:29][CH:28]=1)[NH:25][C:9](=[O:11])[C@@H:8]([CH2:7][C:1](=[O:6])[C:2]([CH3:3])([CH3:4])[CH3:5])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 18611819(R)-alpha-(pivaloylmethyl)hydrocinnamic acidHCID 178419105HCID 178419105, 화합물

생성물 1

HCID 178501427HCID 178501427, 화합물수율 81.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A suspension of 3.0 g (12 mmol) of (R)-α-(pivaloylmethyl)hydrocinnamic acid (see EPA 0,184,550) and 2.66 g (11 mmol) of L-histidine methyl ester dihydrochloride in 340 ml of dimethylformamide was treated at room temperature under a nitrogen atmosphere with 3.45 g (34 mmol) of triethylamine and 4.58 g (12 mmol) of HBTU. The reaction mixture was stirred at room temperature for 5 hours and subsequently evaporated in a high vacuum. The residue was dissolved in 500 ml of ethyl acetate and washed in succession with 100 ml of water, three times with 100 ml of saturated sodium bicarbonate solution each time and with 100 ml of saturated sodium chloride solution. The organic phase was dried over sodium sulfate, evaporated under reduced pressure and the yellowish crude product obtained was chromatographed on silica gel with a 95:5 mixture of methylene chloride and methanol which contained 0.1% ammonia. In this manner there were obtained 3.6 g of N-[(R)-α-(3,3-dimethyl-2-oxobutyl)hydrocinnamoyl]-L-histidine methyl ester as a colourless foam, MS: 399(M)+.

후처리

  1. customsubsequently evaporated in a high vacuum
  2. dissolutionThe residue was dissolved in 500 ml of ethyl acetate
  3. washwashed in succession with 100 ml of water, three times with 100 ml of saturated sodium bicarbonate solution each time
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customthe yellowish crude product obtained
  7. customwas chromatographed on silica gel with a 95:5 mixture of methylene chloride and methanol which

출처 및 근거

ORD 기록
ord-3de8a9a65c14463394a53e6501d7273e
출처 데이터셋
uspto-grants-1994_01
특허 번호
US05278148

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