Isopropylamine → 1-Benzyl 4-tert-butyl 2-[(isopropylamino)carbonyl]piperazine-1,4-dicarboxylate

HRID 1241423Notes

Reaction equation

HRID 1241423 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]1[C:24]([OH:26])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[N:28]1[C:32]2[CH:33]=CC=C[C:31]=2N=N1.Cl.CN(C)CCCN=C=NCC.CN1CCOCC1.C(N)(C)C>CN(C=O)C>[CH:32]([NH:28][C:24]([CH:12]1[CH2:13][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][CH2:16][N:11]1[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])=[O:26])([CH3:33])[CH3:31]

Participants

7

Reactant 5

HCID 6363IsopropylamineHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2756777N-4-Boc-N-1-Cbz-2-piperazine carboxylic acid

Product 1

HCID 210599841-Benzyl 4-tert-butyl 2-[(isopropylamino)carbonyl]piperazine-1,4-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

1-[(benzyloxy)carbonyl]-4-(tert-butoxycarbonyl)piperazine-2-carboxylic acid 47-1 (0.40 g, 1.10 mmol), 1-hydroxybenzotriazole (0.20 g, 1.32 mmol), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (0.27 g, 1.43 mmol), 4-methylmorpholine (0.0.44 g, 4.39 mmol) and isopropyl amine (0.071 g, 1.21 mmol) were dissolved in DMF and stirred at 25° C. for 18 hours. The DMF was then removed under reduced pressure and the residue partitioned between ethyl acetate and dilute aqueous KHSO4. The aqueous phase was drawn off and the organic layer was washed with dilute aqueous NaHCO3, brine, dried, filtered and evaporated to afford 47-2.

Workup

  1. customThe DMF was then removed under reduced pressure
  2. customthe residue partitioned between ethyl acetate and dilute aqueous KHSO4
  3. washthe organic layer was washed with dilute aqueous NaHCO3, brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customto afford 47-2

Sources & evidence

ORD record
ord-8ee0ded6dd8e49ac8d719aeddf23bf90
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

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