Trityl chloride → HCID 57036931, compound

HRID 1078711Notes

Reaction equation

HRID 1078711 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][C@H:9]1[CH:21]([CH2:25][NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22][CH2:23][OH:24])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:41]1([C:47](Cl)([C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:18])[CH3:19])([CH3:15])[CH3:16])[CH2:10][C@H:9]1[CH:21]([CH2:25][NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22][CH2:23][O:24][C:47]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)([C:54]1[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=1)[C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 57202502HCID 57202502, compound

Product 1

HCID 57036931HCID 57036931, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4R)-N-tert-butoxycarbonyl-2-(1-tert-butoxycarbonylaminomethyl-3-hydroxypropyl)-4-tert-butyldimethylsiloxypyrrolidine diastereomer B prepared in REFERENCE EXAMPLE 24-1 (1.01 g, 2 mmol) in methylene chloride (20 ml) were added triethylamine (0.307 ml, 2.2 mmol) and triphenylmethyl chloride (584 mg, 2.1 mmol). The mixture was stirred for 3 h at room temperature under a nitrogen atmosphere. The reaction solution was washed successively with water and saturated aqueous sodium chloride, and dried over anhydrous sodium sulfate. The solvent was removed in vacuo. The residue was subjected to silica gel column chromatography (hexane-ethyl acetate) to give (2S,4S)-N-tert-butoxycarbonyl-2-(1-tert-butoxycarbonylaminomethyl-3-triphenylmethoxypropyl)-4-tert-butyldimethylsiloxypyrrolidine diastereomer B (1.48 g, yield: quantitative).

Workup

  1. washThe reaction solution was washed successively with water and saturated aqueous sodium chloride
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-259a39946e594f82823dd5446db32c04
Source dataset
uspto-grants-1996_08
Patent number
US05550121

Reaction notes

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