Diisopropylethylamine → HCID 11267094, compound

HRID 2054347Notes

Reaction equation

HRID 2054347 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]1[CH2:13][NH:12][C:11](=[O:14])[N:10]2[C:15]3[N:21]=[CH:20][CH:19]=[CH:18][C:16]=3[CH:17]=[C:9]12.Cl[C:23](Cl)([O:25]C(=O)OC(Cl)(Cl)Cl)Cl.NCC(C1NC2C(C=1)=C(OC)C=CN=2)OC1CCCCO1.CCN(C(C)C)C(C)C>C(Cl)Cl>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]1[CH2:13][NH:12][C:11](=[O:14])[N:10]2[C:15]3[N:21]=[CH:20][CH:19]=[C:18]([O:25][CH3:23])[C:16]=3[CH:17]=[C:9]12

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 11185412HCID 11185412, compoundHCID 11346726HCID 11346726, compound

Product 1

HCID 11267094HCID 11267094, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Following the same procedure as for 10a, from triphosgene (20 mg, 0.07 mmol) in CH2Cl2 (3 ml), 9b (58 mg, 0.20 mmol) and DIPEA (34 μl, 0.20 mmol) in CH2Cl2 (3 ml). Reaction time 30 min. at room temperature. The crude mixture was purified by flash column chromatography. Elution with CH2Cl2/MeOH (98/2) gave a diastereomeric mixture (1:1) of 10b (40 g, 63%).

Workup

  1. customReaction time 30 min. at room temperature
  2. customThe crude mixture was purified by flash column chromatography
  3. washElution with CH2Cl2/MeOH (98/2)

Sources & evidence

ORD record
ord-4a5e3db53ad146169284e51616ce9d90
Source dataset
uspto-grants-2008_02
Patent number
US07329666B2

Reaction notes

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