O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → 2-{[(2R)-2-Amino-2-(4-hydroxyphenyl)acetyl]amino}ethane-1-sulfonic acid

HRID 1765334

반응식

HRID 1765334 반응식
C(N([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)CC(O)=O)(OC(C)(C)C)=O.[NH2:20][CH2:21][CH2:22][S:23]([OH:26])(=[O:25])=[O:24].[CH2:27]([N+:31](CCCC)(CCCC)CCCC)[CH2:28]CC.CN(C([O:51]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[NH2:31][C@H:27]([C:13]1[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=1)[C:28]([NH:20][CH2:21][CH2:22][S:23]([OH:26])(=[O:25])=[O:24])=[O:51]

참가 물질

5

반응물 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 21896665Tetrabutylammonium taurineHCID 21896684N-Boc-p-hydroxyphenylglycine

생성물 1

HCID 713630852-{[(2R)-2-Amino-2-(4-hydroxyphenyl)acetyl]amino}ethane-1-sulfonic acid

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

N-Boc-4-hydroxyphenylglycine (1.00 g, 3.21 mmol) was dissolved in DMF (5 ml) and tetrabutylammonium taurine (2.36 g, 6.42 mmol) was added together with additionally 5 ml DMF. The resulting suspension was cooled on ice and TBTU (1.24 g, 3.85 mmol) was added. The ice bath was removed after 30 min and the mixture was stirred for 2 hours before it was filtered and concentrated. TFA in DCM (20%, 20 ml) was added and the reaction mixture was stirred over night. Ethanol (20 ml) was added and the solvents evaporated. The crude product was refluxed in ethanol (100 ml) for 1 hour. Filtration yielded the pure title compound as a white solid, 626 mg (71%). NMR DMSO-d6): 2.4–2.6 (m, 2H),3.2–3.4 (m, 2H),4.79 (s, 1H), 6.78 (d, 2H), 7.23 (d, 2H), 8.22 (t, 1H), 8.4 (brs, 3H), 9.7 (s, 1H).

후처리

  1. additionwas added
  2. customThe ice bath was removed after 30 min
  3. filtrationwas filtered
  4. concentrationconcentrated
  5. additionTFA in DCM (20%, 20 ml) was added
  6. stirringthe reaction mixture was stirred over night
  7. additionEthanol (20 ml) was added
  8. customthe solvents evaporated
  9. temperatureThe crude product was refluxed in ethanol (100 ml) for 1 hour
  10. filtrationFiltration

출처 및 근거

ORD 기록
ord-dd0441e2f89c4612b064616c35b4eae4
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07226943B2

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