p-Toluenesulfonic acid monohydrate → HCID 23257307, compound

HRID 279728Notes

Reaction equation

HRID 279728 reaction equation
COC1C=CC=CC=1C([O:18][CH2:19][C@H:20]1[O:24][C@@H:23]([N:25]2[C:48]3[N:47]=[CH:46][N:45]=[C:29]([NH:30][C:31]([O:33][CH2:34][CH2:35][C:36]4[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][CH:37]=4)=[O:32])[C:28]=3[N:27]=[CH:26]2)[C@H:22]([O:49][C:50](=[O:72])[CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][NH:56][C:57](=[O:71])[CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH3:70])[CH2:21]1)(C1C=CC=CC=1)C1C=CC=CC=1.CC1C=CC(S(O)(=O)=O)=CC=1.O>C(Cl)Cl.CO.C(Cl)Cl>[N+:42]([C:39]1[CH:40]=[CH:41][C:36]([CH2:35][CH2:34][O:33][C:31]([NH:30][C:29]2[C:28]3[N:27]=[CH:26][N:25]([C:48]=3[N:47]=[CH:46][N:45]=2)[C@@H:23]2[O:24][C@H:20]([CH2:19][OH:18])[CH2:21][C@H:22]2[O:49][C:50](=[O:72])[CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][NH:56][C:57](=[O:71])[CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH3:70])=[O:32])=[CH:37][CH:38]=1)([O-:44])=[O:43]

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 131723157HCID 131723157, compound

Product 1

HCID 23257307HCID 23257307, compoundYield 88.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Compound 8 (330 mg, 0.317 mmol) was stirred at r.t. in CH2Cl2/MeOH 4:1 (6 ml) containing 2% of TsOH.H2O for 15 min. Then the mixture was diluted with CH2Cl2 (70 ml) and washed with sat. NaHCO3 soln. (2×40 ml), the aq. phase reextracted with CH2Cl2, the combined org. layer dried (MgSO4) and evaporated, and the residue purified by FC (silica gel, 12×2 cm, CHCl3, CHCl3+5% MeOH). The obtained oily substance was treated with small amounts of Et2O/MeCN 2:1 to give 215 mg (88%) of 10. Amorphous solid. UV (CH2Cl2); 272 (sh, 4.36), 267 (4.41). 1H-NMR (CDCl3):8.71, 8.21-8.15 (2m, H—C(8), H—C(2), 2 H o to NO2,NH(ade)); 7.45 (d, 2 H m to NO2); 6.03 (d, H—C(1′)); 5.58 (m, H—C(2′)); 5.55 (br., NH(CH2)5CO); 5.0 (br., OH—C(5′)); 4.65-4.50 (m, t, H—C(4′), OCH2CH2); 4.12, 3,75 (2m, 2 H—C(5′)); 3.25(q, 1 CH2 of NH(CH2)5CO); 3.15 (t, OCH2CH2);2.9, 2.25 (2m, 2 H—C(3′)); 2.35, 2.15 (2t, 2 CH2 of NH(CH2)5CO), 2 H of Me(CH2)12CO); 1.7-1.15 (m, 28 H, 2 CH2 of NH(CH2)5CO, Me(CH2)12CO); 0.87 (t, Me(CH2)12CO)12 Anal. calc. for C39H57N7O9 ½ H2O (782.02): C 59.90, H 7.41, N 12.54; found: C 60.27, H 7.66, N 12.06.

Workup

  1. washwashed with sat. NaHCO3 soln
  2. dry with materiallayer dried (MgSO4)
  3. customevaporated
  4. customthe residue purified by FC (silica gel, 12×2 cm, CHCl3, CHCl3+5% MeOH)
  5. additionThe obtained oily substance was treated with small amounts of Et2O/MeCN 2:1

Sources & evidence

ORD record
ord-8038bd5aaef448b9b091decab394d2ec
Source dataset
uspto-grants-2002_03
Patent number
US06362171B1

Reaction notes

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