Triphenylphosphine → Phosphoric acid dibenzyl ester 3-oxo-2,3-dihydro-7-oxa-1,2-diazabenzo[de]anthracen-10-ylmethyl ester

HRID 2353187노트

반응식

HRID 2353187 반응식
[OH:1][CH2:2][C:3]1[CH:16]=[CH:15][C:14]2[O:13][C:12]3[C:7]4=[C:8]([C:17](=[O:20])[NH:18][N:19]=[C:6]4[C:5]=2[CH:4]=1)[CH:9]=[CH:10][CH:11]=3.[P:21]([O-])([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>CN(C=O)C>[O:20]=[C:17]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[O:13][C:14]4[CH:15]=[CH:16][C:3]([CH2:2][O:1][P:21](=[O:22])([O:31][CH2:32][C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)[O:23][CH2:24][C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)=[CH:4][C:5]=4[C:6]([C:7]=23)=[N:19][NH:18]1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 4193600DibenzylphosphateHCID 1145979210-Hydroxymethyl-2H-7-oxa-1,2-diaza-benzo[de]anthracen-3-one

생성물 1

HCID 11226277Phosphoric acid dibenzyl ester 3-oxo-2,3-dihydro-7-oxa-1,2-diazabenzo[de]anthracen-10-ylmethyl ester수율 40%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of compound 57 (0.25 mmol) in anhydrous DMF was added dibenzyl phosphate (0.80 mmol) and triphenylphosphine (0.80 mmol). The reaction mixture was stirred while diisopropyl azodicarboxylate was added slowly. The reaction mixture was stirred at room temperature for 3 hours. Solvent was removed in vacuo. To the residue, 100 mL of ethyl acetate was added. The organic layer was washed with water and brine, then dried with MgSO4. The Solvents were removed to afford a yellow oil. The oil was re-crystallized in EtOAc/Hexanes to afford an off-white solid 60 in 40% yield. MS (ES+): 527; Mp: 223-225° C.; 1H-NMR (CDCl3, 400 MHz): 9.91 (s, 1H), 8.13 (d, J=2.0 Hz, 1H), 8.11 (dd, J=8.0 and 1.0 Hz, 1H), 7.85 (t, J=8.0 Hz, 1H), 7.59 (dd, J=8.0 and 1.0 Hz, 1H), 7.45 (dd, J=8.5 and 1.0 Hz, 1H), 7.36-7.26 (m, 11H), 5.08 (m, 6H). Anal. Calcd. for C29H23N2O6P.(0.15hydrazine): C, 65.56; H, 4.48; N, 6.06. Found: C, 65.55; H, 4.33; N, 6.09.

후처리

  1. additionwas added slowly
  2. customSolvent was removed in vacuo
  3. additionTo the residue, 100 mL of ethyl acetate was added
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried with MgSO4
  6. customThe Solvents were removed
  7. customto afford a yellow oil
  8. customThe oil was re-crystallized in EtOAc/Hexanes

출처 및 근거

ORD 기록
ord-751633b19cb34b80be16f90ef900af42
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07750008B2

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