1,2-Dichloroethane → HCID 117748782, 화합물

HRID 1775862노트

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HRID 1775862 반응식
[C:1]([O:5][C:6](=[O:37])[C@@H:7]([NH:24][C:25](=[O:36])[C:26]1[CH:31]=[CH:30][C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:28][CH:27]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:20]=[CH:19][C:18]([C:21]([OH:23])=O)=[CH:17][N:16]=2)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.[C:42]([NH:50][NH2:51])(=[O:49])[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48]>C(Cl)Cl.CN(C1C=CN=CC=1)C.C([O-])(O)=O.[Na+]>[C:32]([C:29]1[CH:28]=[CH:27][C:26]([C:25]([NH:24][C@@H:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[N:20]=[CH:19][C:18]([C:21]([NH:51][NH:50][C:42](=[O:49])[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])=[O:23])=[CH:17][N:16]=3)=[CH:11][CH:10]=2)[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:37])=[O:36])=[CH:31][CH:30]=1)([CH3:34])([CH3:33])[CH3:35]

참가 물질

7

반응물 3

HCID 111,2-DichloroethaneHCID 240032HeptanohydrazideHCID 117740712(S)-2-(4-(3-(tert-butoxy)-2-(4-(tert-butyl)benzamido)-3-oxopropyl)phenyl)pyrimidine-5-carboxylic acid

생성물 1

HCID 117748782HCID 117748782, 화합물수율 61%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매HCID 516892Sodium Bicarbonate용매

실험 절차

Prepared using General Procedure 7. Into a stirring solution of (S)-2-(4-(3-(tert-butoxy)-2-(4-(tert-butyl)benzamido)-3-oxopropyl)phenyl)pyrimidine-5-carboxylic acid (50 mg, 0.10 mmol) in DCM (2 mL) were added EDC (34 mg, 0.20 mmol), DMAP (3 mg, 0.02 mmol) and heptanehydrazide (16 mg, 0.11 mmol). After 18 h, the reaction mixture was diluted with NaHCO3 and extracted with DCM (2×). The organic layers were combined, dried (Na2SO4), concentrated and purified by chromatography (EA/Hexane) to provide 38 mg (61%) of tert-butyl (S)-2-(4-(tert-butyl)benzamido)-3-(4-(5-(2-heptanoylhydrazine-1-carbonyl)pyrimidin-2-yl)phenyl)propanoate. LCMS-ESI (m/z) calculated for C36H47BN5O5: 629.8; no m/z observed, tR=3.84 min (Method 1). 1H NMR (400 MHz, CDCl3) δ 9.17 (s, 2H), 8.42 (d, J=8.2 Hz, 2H), 7.69 (d, J=8.4 Hz, 2H), 7.43 (d, J=8.4 Hz, 2H), 7.34 (d, J=8.2 Hz, 2H), 6.70 (d, J=7.3 Hz, 1H), 5.01 (dd, J=12.6, 5.8 Hz, 1H), 3.41-3.20 (m, 2H), 2.35 (t, J=7.5 Hz, 2H), 1.81-1.61 (m, 2H), 1.59 (d, J=14.0 Hz, 2H), 1.45 (s, 4H), 1.42-1.22 (m, 18H), 0.88 (t, J=6.8 Hz, 3H).

후처리

  1. customPrepared
  2. extractionextracted with DCM (2×)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified by chromatography (EA/Hexane)

출처 및 근거

ORD 기록
ord-fd116598c21d421d89cdda580674ff25
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09260427B2

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