Ethyl chloroformate → HCID 68790168, compound

HRID 1713596Notes

Reaction equation

HRID 1713596 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[CH:11][CH:10]=2)=[CH:6][C:5]2[C@@:17]3([CH2:28][O:29][C:4]=2[CH:3]=1)[C@H:22]([OH:23])[C@@H:21]([OH:24])[C@H:20]([OH:25])[C@@H:19]([CH2:26][OH:27])[O:18]3.Cl[C:31]([O:33][CH2:34][CH3:35])=[O:32]>N1C(C)=CC(C)=CC=1C.C(Cl)Cl>[C:31](=[O:32])([O:33][CH2:34][CH3:35])[O:27][CH2:26][C@H:19]1[O:18][C@@:17]2([C:5]3[CH:6]=[C:7]([CH2:8][C:9]4[CH:10]=[CH:11][C:12]([CH2:15][CH3:16])=[CH:13][CH:14]=4)[C:2]([Cl:1])=[CH:3][C:4]=3[O:29][CH2:28]2)[C@H:22]([OH:23])[C@@H:21]([OH:24])[C@@H:20]1[OH:25]

Participants

5

Reactant 2

HCID 10928Ethyl chloroformate2×HCID 25154393HCID 25154393, compound

Product 1

HCID 68790168HCID 68790168, compoundYield 53.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 79532,4,6-TrimethylpyridineSolvent

Procedure

To a solution of 30 (12 mg, 28.5 μmol) in 2,4,6-collidine (100 μL) at −30° C. was added a solution of ethyl chloroformate (4 μL, 41.8 umol, 1.5 eq.) in DCM (100 μL). The mixture was kept at −30° C. for 1.5 hours, warmed to ambient temperature, and stirred overnight, after which additional ethylchloroformate (4 μL) was added. The reaction mixture was quenched with methanol, evaporated, and purified via HPLC to give 31 (7.5 mg, 53% yield). 1H NMR (300 MHz, CD3OD) δ 7.14 (s, 1H), 7.07 (s, 4H), 6.83 (s, 1H), 4.68 (d, J=10.2 Hz, 1H), 4.57 (d, J=10.5 Hz, 1H), 4.36 (dd, J=2.1, 11.4 Hz, 1H), 4.21 (dd, J=5.1, 11.4 Hz, 1H), 4.08 (q, J=7.2 Hz, 2H), 3.99 (s, 2H), 3.71 (d, J=9.6 Hz, 1H), 3.53-3.59 (m, 1H), 3.39 (t, J=8.7 Hz, 1H), 3.27-3.34 (m, 1H), 2.58 (q, J=7.5 Hz, 2H), 1.17-1.23 (m, 6H).

Workup

  1. customThe reaction mixture was quenched with methanol
  2. customevaporated
  3. custompurified via HPLC

Sources & evidence

ORD record
ord-8e59184eff2c454cbef4a93e91ed434c
Source dataset
uspto-grants-2010_09
Patent number
US07795228B2

Reaction notes

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