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Trifluoroacetic acid → (R)-1-(4-dodecylbenzoyl)pyrrolidine-2-carbonitrile

HRID 1484091
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HRID 1484091 반응식
[C:1]([C@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10]C(C)(C)C)=O)#[N:2].FC(F)(F)C(O)=O.[CH2:22]([C:34]1[CH:42]=[CH:41][C:37](C(O)=O)=[CH:36][CH:35]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>ClCCl>[CH2:22]([C:34]1[CH:35]=[CH:36][C:37]([C:8]([N:4]2[CH2:5][CH2:6][CH2:7][C@@H:3]2[C:1]#[N:2])=[O:10])=[CH:41][CH:42]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]
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참가 물질

7

반응물 5

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 4133114-Dodecylbenzoic acidHCID 2724699PyBOPHCID 2756788tert-butyl (2R)-2-cyanopyrrolidine-1-carboxylate

생성물 1

HCID 53248516(R)-1-(4-dodecylbenzoyl)pyrrolidine-2-carbonitrile수율 39.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

General procedure D was used to deprotect 1.4 mmols of 41 using 14 mL of dichloromethane and trifluoroacetic acid. After previously described recrystallization techniques, the TFA salt of 41 was coupled to 0.4 grams (1.4 mmols) of 4-dodecylbenzoic acid using 0.73 grams (1.4 mmols) of PyBOP and 0.72 grams (5.6 mmols) of N,N-diisopropylethylamine in 14 mL of dichloromethane according to general procedure E. Using previously described work-up and purification techniques (column chromatography, 25% EtOAc in hexanes), yielded 0.2 grams (0.55 mmols, 39%) of the title product as an off-white solid. 1H and 13C NMR data were identical to that of 29.

후처리

  1. customAfter previously described recrystallization techniques
  2. customwork-up and purification techniques (column chromatography, 25% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-8578b2e9775f4dc9abbc0d363edf4e0d
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09421177B2

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