9-Fluorenylmethyl chloroformate → N-Fmoc-2-(trans-Dec-4-en-1-ylamino)acetaldehyde dimethyl acetal

HRID 1661858Notes

Reaction equation

HRID 1661858 reaction equation
[CH3:1][O:2][CH:3]([O:16][CH3:17])[CH2:4][NH:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]/[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].C(N(C(C)C)CC)(C)C.[C:27](Cl)([O:29][CH2:30][CH:31]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:37]2[C:32]1=[CH:33][CH:34]=[CH:35][CH:36]=2)=[O:28].OS([O-])(=O)=O.[K+]>ClCCl>[CH3:17][O:16][CH:3]([O:2][CH3:1])[CH2:4][N:5]([CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]/[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:27]([O:29][CH2:30][CH:31]1[C:32]2[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:38]2[C:43]1=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:28]

Participants

6

Reactant 4

HCID 343679-Fluorenylmethyl chloroformateHCID 81531DiisopropylethylamineHCID 516920Potassium bisulfateHCID 219663022-(trans-Dec4-en-1-ylamino)acetaldehyde dimethyl acetal

Product 1

HCID 21966301N-Fmoc-2-(trans-Dec-4-en-1-ylamino)acetaldehyde dimethyl acetalYield 80.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(trans-Dec-4-en-1-ylamino)acetaldehyde dimethyl acetal (10.5 g, 43.2 mmol) was mixed with dichloromethane (300 mL) and 7.5 mL (43.2 mmol) diisopropylethyl amine and 11.2 g (43.2 mmol) of FMOC-Cl was added portionwise. The reaction was stirred at room temperature for 3 hours and then poured into a solution of 10% KHSO4 (200 mL). The organic layer was washed with water (200 mL), dried over MgSO4, and concentrated under reduced pressure. The resulting oil was chromatographed on silica gel in 10% EtOAc/Hexanes to give 16.1 g (34.6 mmol) of N-Fmoc-2-(trans-dec-4-en-1-ylamino)acetaldehyde dimethyl acetal as a clear oil that was used directly in the next step.

Workup

  1. additionwas added portionwise
  2. washThe organic layer was washed with water (200 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting oil was chromatographed on silica gel in 10% EtOAc/Hexanes

Sources & evidence

ORD record
ord-f6e72a8b186d4d31b6b8f03d9f520aa8
Source dataset
uspto-grants-2011_10
Patent number
US08030445B2

Reaction notes

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