Water → HCID 21462368, compound

HRID 1940489Notes

Reaction equation

HRID 1940489 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[F:20][C:21]1[C:34]([NH:35][C:36]([CH:38]2[NH:43][CH2:42][CH:41]3[CH:39]2[CH2:40]3)=[O:37])=[CH:33][C:24]2[N:25]([CH2:30][C:31]#[CH:32])[C:26](=[O:29])[CH2:27][O:28][C:23]=2[CH:22]=1.O>C(Cl)Cl>[F:20][C:21]1[C:34]([N:35]2[C:36](=[O:37])[CH:38]3[CH:39]4[CH2:40][CH:41]4[CH2:42][N:43]3[C:2]2=[O:4])=[CH:33][C:24]2[N:25]([CH2:30][C:31]#[CH:32])[C:26](=[O:29])[CH2:27][O:28][C:23]=2[CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 94429TriphosgeneHCID 21462366HCID 21462366, compound

Product 1

HCID 21462368HCID 21462368, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of triphosgene (57 mg) in CH2Cl2 (1 mL) was added dropwise to a stirred solution of triethylamine (0.2 mL) and the compound of Step G, Example 3, (190 mg) in CH2Cl2 (50 mL) under N2 at room temperature. The solution was stirred at room temperature for 20 minutes. 30 mL of water was added. The organic layer was separated, dried (MgSO4) and evaporated to dryness. Flash chromatography yielded the title compound of Step H, a compound of the invention, as a white solid (127 mg), 62%; m.p. 217°-219° C.; IR (nujol, cm-1): 3253.6 and 2129.3 (C≡C), 1625 and 1715 (C=O).

Workup

  1. customat room temperature
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-6534fa4b8d934dfb9f0cb24a0493e3b9
Source dataset
uspto-grants-1997_12
Patent number
US05700761

Reaction notes

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