Dimethylformamide → HCID 86752688, compound

HRID 962869Notes

Reaction equation

HRID 962869 reaction equation
Cl.CN(C)[CH2:4][CH2:5][CH2:6]N=C=NCC.[C:13]([O:17]C(N1CCC(CCC(O)=O)CC1)=O)([CH3:16])([CH3:15])[CH3:14].C([N:34]([CH:37]([CH3:39])[CH3:38])[CH2:35][CH3:36])(C)C.[OH:40]N1C2C=CC=CC=2N=N1.[C:50]([O:54][CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)(=[O:53])[NH:51][NH2:52].CN([CH:65]=[O:66])C>>[C:13]([O:17][N:34]1[CH2:35][CH2:36][CH:4]([CH2:5][CH2:6][C:65]([NH:52][NH:51][C:50]([O:54][CH2:55][C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)=[O:53])=[O:66])[CH2:39][C:37]1=[C:38]=[O:40])([CH3:14])([CH3:15])[CH3:16]

Participants

7

Reactant 6

HCID 6228Dimethylformamide2×HCID 757711-HydroxybenzotriazoleHCID 79242Benzyl carbazateHCID 81531DiisopropylethylamineHCID 15125403-(1-((Tert-butoxy)carbonyl)piperidin-4-yl)propanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 86752688HCID 86752688, compound

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (380 mg) was added to a mixture of the product of step (a) (0.5 g), diisopropylethylamine (0.34 ml), 1-hydroxybenztriazole (333 mg) and DMF (10 ml) at ambient temperature. The mixture was stirred for 5 minutes and benzyl carbazate (325 mg) in DMF (2 ml) was added. The mixture was stirred for 18 hours at ambient temperature. The solvent was removed by evaporation and the residue was partitioned between ice-water (25 ml) containing 1M sodium hydroxide (2 ml) and ethyl acetate (50 ml). The ethyl acetate extract was washed with water (20 ml), 0.25M citric acid solution (20 ml), water (20 ml) and saturated sodium chloride solution (10 ml) and dried (MgSO4). The solvent was removed by evaporation to give benzyl 3-[3-(1-t-butoxy-carbonylpiperidin-4-yl) propanoyl]carbazate as a foam (790 mg); NMR Spectrum (d6 --DMSO) 0.8-1.1 (m, 2H), 1.3-1.5 (m, 12H), 1.6 (br d, 2H), 2.1 (br t, 2H), 2.62 (m, 2H), 3.9 (br d, 2H), 5.07 (s, 2H), 7.32 (s, 5H), 9.08 (s, 1H), 9.6 (s, 1H).

Workup

  1. stirringThe mixture was stirred for 18 hours at ambient temperature
  2. customThe solvent was removed by evaporation
  3. customthe residue was partitioned between ice-water (25 ml)
  4. additioncontaining 1M sodium hydroxide (2 ml) and ethyl acetate (50 ml)
  5. extractionThe ethyl acetate extract
  6. washwas washed with water (20 ml), 0.25M citric acid solution (20 ml), water (20 ml) and saturated sodium chloride solution (10 ml)
  7. dry with materialdried (MgSO4)
  8. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-a5a2b975493449949a0051a21d853e54
Source dataset
uspto-grants-1998_06
Patent number
US05760057

Reaction notes

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