Dimethylamine → HCID 72455647, 화합물

HRID 1504835노트

반응식

HRID 1504835 반응식
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C@@H:13]([C:22]([OH:24])=O)[NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25][N:26](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)[CH3:27].F[P-](F)(F)(F)(F)F.CNC.C(N(CC)CC)C>CN(C=O)C.O>[C:18]([O:17][C:15]([NH:14][CH:13]([C:22]([N:26]([CH3:27])[CH3:25])=[O:24])[CH2:12][NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:16])([CH3:19])([CH3:20])[CH3:21]

참가 물질

7

반응물 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 2755950Boc-dap(Z)-OHHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

생성물 1

HCID 72455647HCID 72455647, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-{[(benzyloxy)carbonyl]amino}-N-(tert-butoxycarbonyl)alanine (10.0 g, 30.0 mmol) in DMF (100 mL) was added HATU (14.0 g, 36.0 mmol). After 2 hours, dimethylamine (4.9 g, 60 mmol) and triethylamine (15.0 g, 149 mmol) were added. After 16 hours, the reaction mixture was diluted with water and the aqueous layer was extracted with ethyl acetate (3×100 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by reverse phase HPLC (acetonitrile/water gradient) to give benzyl {2-[(tert-butoxycarbonyl)amino]-3-(dimethylamino)-3-oxopropyl}carbamate. MS ESI calc'd. for C18H28N3O5 [M+H]+ 366. found 366. 1H NMR (400 MHz, CD3OD) δ 7.33-7.31 (m, 5H), 5.31-5.20 (m, 2H), 4.61-4.48 (m, 1H), 2.93 (s, 3H), 2.87 (s, 3H), 2.74-2.71 (m, 1H), 2.71-2.68 (m, 1H), 1.43 (s, 9H).

후처리

  1. waitAfter 16 hours
  2. extractionthe aqueous layer was extracted with ethyl acetate (3×100 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by reverse phase HPLC (acetonitrile/water gradient)

출처 및 근거

ORD 기록
ord-a50784830ad34aef873efecd5a2436c2
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216173B2

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