Triethylamine → HCID 86612489, compound

HRID 2118223Notes

Reaction equation

HRID 2118223 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[C:18]2[CH:23]=[CH:22][C:21](/[CH:24]=[CH:25]/[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[CH:20][CH:19]=2)=[C:9](\[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)/[CH2:10][CH3:11])=[CH:4][CH:3]=1.CCN(CC)CC.Cl[C:41]([O:43][CH2:44][CH3:45])=[O:42]>C(Cl)Cl>[CH2:44]([O:43][C:41]([O:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[C:18]2[CH:19]=[CH:20][C:21](/[CH:24]=[CH:25]/[C:26]([O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:27])=[CH:22][CH:23]=2)=[C:9](\[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)/[CH2:10][CH3:11])=[CH:4][CH:3]=1)=[O:42])[CH3:45]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 58877662HCID 58877662, compound

Product 1

HCID 86612489HCID 86612489, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl ester 12 (0.45 g, 1.06 mmol) in CH2Cl2 (20 mL) at 0° C. was added Et3N (0.32 mL, 0.23 g, 2.33 mmol) and ethyl chloroformate (0.115 mL, 0.126 g, 1.16 mmol) and the mixture stirred at ambient temperature for 1 h. The mixture was washed with ice-chilled 0.1 N hydrochloric acid and the organic layer dried (Na2SO4) and evaporated to provide compound 39 as an off-white solid (0.52 g, 99%); 1H NMR (DMSO-d6): δ 0.86 (t, J=7.1 Hz, 3H), 1.23 (t, J=7.5 Hz, 3H), 1.48 (s, 9H), 2.40 (q, J=7.5 Hz, 2H), 4.17 (q, J=7.1 Hz, 2H), 6.51 (d, J=16 Hz, 1H), 6.87 (d, J=9 Hz, 2H), 6.91 (d, J=9 Hz, 2H), 7.10-7.16 (m, 3H), 7.18-7.22 (m, 2H), 7.25 (d, J=8.1 Hz, 2H), 7.55 (d, J=16 Hz, 1H), 7.71 (d, J=8.1 Hz, 2H); MS, m/z 521 (M+Na)+.

Workup

  1. washThe mixture was washed with ice-
  2. temperaturechilled 0.1 N hydrochloric acid
  3. dry with materialthe organic layer dried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-f5240e2615dc4c4d8f3030a41f8dc718
Source dataset
uspto-grants-2008_10
Patent number
US07442833B2

Reaction notes

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