HCID 57115323, compound → HCID 57314490, compound

HRID 742931Notes

Reaction equation

HRID 742931 reaction equation
[Si]([O:8][CH2:9][CH2:10][O:11][C:12]([NH:14][C@H:15]([C@@H:23]([OH:47])[CH2:24][C@@H:25]([NH:33][C:34]([O:36][CH2:37][CH2:38][O:39][Si](C(C)(C)C)(C)C)=[O:35])[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:13])(C(C)(C)C)(C)C>CO.C[Si](Cl)(C)C>[OH:8][CH2:9][CH2:10][O:11][C:12]([NH:14][C@H:15]([C@@H:23]([OH:47])[CH2:24][C@@H:25]([NH:33][C:34]([O:36][CH2:37][CH2:38][OH:39])=[O:35])[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:13]

Participants

4

Reactant 1

HCID 57115323HCID 57115323, compound

Product 1

HCID 57314490HCID 57314490, compoundYield 578.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6397ChlorotrimethylsilaneSolvent

Procedure

In two batches, 81.4 mg (0.016 mmol) of the compound from Example 335B above was dissolved in 2 mL of methanol to which 14.9 μL of trimethylsilyl chloride was added and stirred for 2 hours. The solvent was removed and the crude product chromatographed on silica gel, eluting with 2% and 5% methanol in methylene chloride. The solvent was removed and the product dried to afford 42.6 mg of the title compound. MS M/Z (DCI/NH3): 461 (M+H), 478 (M+NH4). Proton NMR (DMSO): δ1.46 (t, 2H), 2.53-2.77 (4H), 3.45 (m, 3H), 3.55 (d, 1H), 3.64-3.92 (6H), 4.64 (m, 2H), 6.65 (d, 1H), 6.94 (d, 1H), 7.07-7.27 (10H). Anal calc. for C24H32N2O7 ·H2O: C, 60.25; H, 7.11; N, 5.86; found: C, 60.38; H, 6.56; N, 5.86.

Workup

  1. additionwas added
  2. customThe solvent was removed
  3. customthe crude product chromatographed on silica gel
  4. washeluting with 2% and 5% methanol in methylene chloride
  5. customThe solvent was removed
  6. customthe product dried

Sources & evidence

ORD record
ord-03493dc2546148cfa2bf042eb83f50c4
Source dataset
uspto-grants-1996_09
Patent number
US05554783

Reaction notes

Loading…