Toluene → HCID 69624811, compound

HRID 1386911Notes

Reaction equation

HRID 1386911 reaction equation
[C:1]([NH:18][C@H:19]([C:41]([OH:43])=[O:42])[CH2:20][S:21][C:22]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([O:3][CH2:4]C1C2C(=CC=CC=2)C2C1=CC=CC=2)=[O:2].[C:44]1([CH3:50])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>>[C:29]([O:43][C:41](=[O:42])[C@H:19]([CH2:20][S:21][C:22]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[NH:18][C:1]([O:3][CH2:4][C:48]1[C:49]2[CH2:26][C:25]3[C:50](=[CH:27][CH:28]=[CH:23][CH:24]=3)[C:44]=2[CH:45]=[CH:46][CH:47]=1)=[O:2])([CH3:34])([CH3:30])[CH3:22]

Participants

3

Reactant 2

HCID 1140TolueneHCID 128239N-((9H-Fluoren-9-ylmethoxy)carbonyl)-S-(triphenylmethyl)-L-cysteine

Product 1

HCID 69624811HCID 69624811, compound

Conditions

Temperature
80 °C

Procedure

A suspension of Fmoc-S-trityl-L-cysteine (2.9 g, 5 mmol) in dry toluene (10 mL) was heated to 80° C. To this suspension was added over 20 min., di-tert-butyl-dimethylformamide acetal (4.8 mL, 20 mmol). The solution was cooled, washed with water, saturated sodium bicarbonate (2×10 mL), and evaporated. The residue was purified by flash chromatography eluting with ethyl acetate/hexanes (15/85), to give 2.2 g of N-Fluorenylmethoxycarbonyl-S-trityl-L-Cysteine-t-butyl ester.

Workup

  1. additionTo this suspension was added over 20 min.
  2. temperatureThe solution was cooled
  3. washwashed with water, saturated sodium bicarbonate (2×10 mL)
  4. customevaporated
  5. customThe residue was purified by flash chromatography
  6. washeluting with ethyl acetate/hexanes (15/85)

Sources & evidence

ORD record
ord-2248f7e9bb0344188d7bfea7d5f34580
Source dataset
uspto-grants-2001_07
Patent number
US06265572B1

Reaction notes

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