HCID 18939621, compound → (2S,3S,5S)-2,5-Bis-(N-(3-hydroxy-1-propoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane

HRID 52849Notes

Reaction equation

HRID 52849 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]([NH:15][CH:16]([CH:24]([OH:49])[CH2:25][CH:26]([NH:34][C:35]([O:37][CH2:38][CH2:39][CH2:40][O:41][Si](C(C)(C)C)(C)C)=[O:36])[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:14])(C(C)(C)C)(C)C>CO.C[Si](Cl)(C)C>[OH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]([NH:15][C@H:16]([C@@H:24]([OH:49])[CH2:25][C@@H:26]([NH:34][C:35]([O:37][CH2:38][CH2:39][CH2:40][OH:41])=[O:36])[CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:14]

Participants

4

Reactant 1

HCID 18939621HCID 18939621, compound

Product 1

HCID 22871564(2S,3S,5S)-2,5-Bis-(N-(3-hydroxy-1-propoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexaneYield 19.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6397ChlorotrimethylsilaneSolvent

Procedure

A 0.170 g (0.237 mmol) of the compound from Example 337B above was dissolved in 2 mL of methanol to which 30 μL of trimethylsilyl chloride was added and stirred for 2.25 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 22.7 mg of the title compound. MS M/Z (DCI/NH3): 489 (M+H), 506 (M+NH4). Proton NMR (DMSO): δ 1.45 (t, 2H), 1.60 (m, 4H), 2.55-2.75 (4H), 3.40 (m, 2H), 3.55 (br, 1H), 3.74-3.96 (18H), 4.44 (t, 2H), 4.62 (d, 1H), 6.63 (d, 1H), 6.89 (d, 1H), 7.07-7.27 (10H).

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-e9df3e2f3e1f40b8a0ac6de78ee30509
Source dataset
uspto-grants-1997_04
Patent number
US05616714

Reaction notes

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