Hydrochloric Acid → HCID 67270563, 화합물

HRID 1695543노트

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HRID 1695543 반응식
[OH:1][C@@H:2]1[C@H:15]2[C@@H:6]([CH2:7][CH2:8][C:9]3[C@:14]2([CH3:16])[CH2:13][CH:12]([CH:17]=O)[C:11](=O)[CH:10]=3)[C@@H:5]2[CH2:20][CH2:21][C@:22]3([C:26]4([CH2:30][O:29][CH2:28][O:27]4)[O:25][CH2:24][O:23]3)[C@@:4]2([CH3:31])[CH2:3]1.[NH:32]([C:34]1[CH:35]=[C:36]([CH:40]=[CH:41][CH:42]=1)[C:37]([OH:39])=[O:38])[NH2:33].C([O-])(=O)C.[K+].Cl>C(O)C.O>[OH:1][C@H:2]1[C@@H:15]2[C@H:6]([CH2:7][CH2:8][C:9]3[C@@:14]2([CH3:16])[CH2:13][C:12]2[CH:17]=[N:33][N:32]([C:34]4[CH:35]=[C:36]([CH:40]=[CH:41][CH:42]=4)[C:37]([OH:39])=[O:38])[C:11]=2[CH:10]=3)[C@H:5]2[CH2:20][CH2:21][C@@:22]3([C:26]4([CH2:30][O:29][CH2:28][O:27]4)[O:25][CH2:24][O:23]3)[C@:4]2([CH3:31])[CH2:3]1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 517044Potassium AcetateHCID 27365213-Hydrazinobenzoic acidHCID 59810282HCID 59810282, 화합물

생성물 1

HCID 67270563HCID 67270563, 화합물수율 106.9%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

(8S,9S,10R,11S,13S,14S,17R)-11-hydroxy-10,13-dimethyl-3-oxo-1,2,3,6,7,8,9,10,11,12,13,14,15,16-tetradecahydrodispiro[cyclopenta[a]phenanthrene-17,4′-[1,3]dioxolane-5′,4″-[1,3]dioxolane]-2-carbaldehyde (Steroids 2003, (68), 177-191) (1.4 g, 3.24 mmol) was dissolved in ethanol (10 ml) and water (1 ml). 3-hydrazinobenzoic acid (0.493 g, 3.24 mmol) and potassium acetate (0.491 g, 5 mmol) were added to give a brown solution which was stirred for 1 hour at room temperature. The mixture was poured into a separation funnel containing 1M HCl (200 ml) and was extracted with DCM (3 times 150 ml). The combined organic phases were washed with water (2 times 100 ml) and 1M NaOH. The organic phase was washed with brine, dried over Na2SO4, filtered and the solvent was evaporated to give 1.9 g of a brownish foam. The crude product was purified on a silica gel column (Heptane:EtOAc=1:1) and the product containing fractions were evaporated under reduced pressure to yield 1.5 g of the desired compound. APCI-MS m/z: 549 [MH+].

후처리

  1. customto give a brown solution which
  2. additionThe mixture was poured into a separation funnel
  3. extractionwas extracted with DCM (3 times 150 ml)
  4. washThe combined organic phases were washed with water (2 times 100 ml) and 1M NaOH
  5. washThe organic phase was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-6493fd6cf970400e94d784ec9fc9b167
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163724B2

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