Diisopropylethylamine → HCID 70114104, compound

HRID 324409Notes

Reaction equation

HRID 324409 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH:13]=[C:12]([CH:14]3[C:20]4[N:21]=[C:22]([CH3:24])[O:23][C:19]=4[CH:18]=[CH:17][C:16]4[CH:25]=[C:26]([O:29][Si](C(C)(C)C)(C)C)[CH:27]=[CH:28][C:15]3=4)[C:11](=[O:37])[NH:10][C:9]2=[O:38])[CH:5]=[CH:4][N:3]=1.[NH:39]1[CH2:42][CH:41]([C:43]([OH:45])=[O:44])[CH2:40]1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[OH:29][C:26]1[CH:27]=[CH:28][C:15]2[CH:14]([C:12]3[C:11](=[O:37])[NH:10][C:9](=[O:38])[N:8]([C:6]4[CH:5]=[CH:4][N:3]=[C:2]([N:39]5[CH2:42][CH:41]([C:43]([OH:45])=[O:44])[CH2:40]5)[N:7]=4)[CH:13]=3)[C:20]3[N:21]=[C:22]([CH3:24])[O:23][C:19]=3[CH:18]=[CH:17][C:16]=2[CH:25]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 931923-azetidinecarboxylic AcidHCID 88152681HCID 88152681, compound

Product 1

HCID 70114104HCID 70114104, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from step (ix) was treated with 3-azetidinecarboxylic acid (0.096 g) and N,N-diisopropylethylamine (0.445 ml) in N,N-dimethylformamide (10 ml) at 85° C. for 4 hours. The mixture was partitioned between 1N HCl and ethyl acetate. The aqueous layer was adjusted to pH 6 and extracted with ethyl acetate. The organic phase was dried (MgSO4) and evaporated under reduced pressure to give a solid. Purification was by reverse phase chromatography eluting with 50% methanol in 0.1% aqueous ammonium acetate solution.

Workup

  1. customThe mixture was partitioned between 1N HCl and ethyl acetate
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customevaporated under reduced pressure
  5. customto give a solid
  6. customPurification
  7. washeluting with 50% methanol in 0.1% aqueous ammonium acetate solution

Sources & evidence

ORD record
ord-bf5a0c3f52d04e8dac7e7b5326101291
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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