Diisopropylethylamine → HCID 18689692, compound

HRID 1872019Notes

Reaction equation

HRID 1872019 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH:13]=[C:12]([CH:14]3[C:20]4[CH:21]=[CH:22][C:23]([CH2:25][CH3:26])=[CH:24][C:19]=4[CH:18]=[CH:17][C:16]4[CH:27]=[C:28]([O:31][Si](C(C)(C)C)(C)C)[CH:29]=[CH:30][C:15]3=4)[C:11](=[O:39])[NH:10][C:9]2=[O:40])[CH:5]=[CH:4][N:3]=1.[C:41]([CH:44]1[CH2:47][NH:46][CH2:45]1)([OH:43])=[O:42].C(N(CC)C(C)C)(C)C>CN1CCCC1=O>[CH2:25]([C:23]1[CH:24]=[CH:19][C:20]2[CH:14]([C:12]3[C:11](=[O:39])[NH:10][C:9](=[O:40])[N:8]([C:6]4[CH:5]=[CH:4][N:3]=[C:2]([N:46]5[CH2:47][CH:44]([C:41]([OH:43])=[O:42])[CH2:45]5)[N:7]=4)[CH:13]=3)[C:15]3[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][C:16]=3[CH:17]=[CH:18][C:21]=2[CH:22]=1)[CH3:26]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 931923-azetidinecarboxylic AcidHCID 18689769HCID 18689769, compound

Product 1

HCID 18689692HCID 18689692, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of the product from step (viii) (0.5 g), 3-carboxyazetidine (0.13 g) and N,N-diisopropylethylamine (0.52 ml) in 1-methyl-2-pyrrolidinone (10 ml) was heated at 90° C. for 6 hours and partitioned between ethyl acetate and 1M HCl. The organic phase was washed with water, dried (MgSO4) and concentrated in vacuo to 10 ml. Isohexane (5 ml) was added and the product was collected by filtration. Yield 0.25 g.

Workup

  1. custompartitioned between ethyl acetate and 1M HCl
  2. washThe organic phase was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo to 10 ml
  5. additionIsohexane (5 ml) was added
  6. filtrationthe product was collected by filtration

Sources & evidence

ORD record
ord-27003955cc81478c836b6d0c03a1a478
Source dataset
uspto-grants-2000_08
Patent number
US06107297

Reaction notes

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