Triethylamine → HCID 18727277, compound

HRID 609708Notes

Reaction equation

HRID 609708 reaction equation
[C:1]([O:5][NH:6][C:7]([C@H:9]1[CH2:14][NH:13][CH2:12][CH2:11][N:10]1[S:15]([N:18]1[CH2:23][CH2:22][CH:21]([C:24](=[O:32])[C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)[CH2:20][CH2:19]1)(=[O:17])=[O:16])=[O:8])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:40]([N:44]=[C:45]=[O:46])([CH3:43])([CH3:42])[CH3:41]>C(Cl)Cl>[C:1]([O:5][NH:6][C:7]([C@H:9]1[CH2:14][N:13]([C:45]([NH:44][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:46])[CH2:12][CH2:11][N:10]1[S:15]([N:18]1[CH2:19][CH2:20][CH:21]([C:24](=[O:32])[C:25]2[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=2)[CH2:22][CH2:23]1)(=[O:17])=[O:16])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62412tert-Butyl isocyanateHCID 18727272HCID 18727272, compound

Product 1

HCID 18727277HCID 18727277, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-tert-butoxy-1-[4-(4-chlorobenzoyl)piperidine-1-sulfonyl]piperazine-2-(R)-carboxamide [prepared as described in Example 15, above] (600 mg, 1.23 mmol) in methylene chloride (8 ml) was added triethylamine (0.15 ml, 1.1 mmol) and tert-butyl-isocyanate (0.15 ml, 1.33 mmol). The reaction was stirred for 4 h, concentrated in vacuo, and the residue was chromatographed (SiO2, PTLC, 50% ethyl acetate/hexanes) to give N-tertbutoxy-4-tert-butylaminocarbonyl-1-[4-(4-chlorobenzoyl)piperidine-1-sulfonyl]piperazine-2-(R)-carboxamide (75%) as a clear oil.

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue was chromatographed (SiO2, PTLC, 50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-21559568db1e45f69580be946d7572d2
Source dataset
uspto-grants-1999_12
Patent number
US05998412

Reaction notes

Loading…