Diisopropylethylamine → tert-Butyl (((2S,3R)-3-methyl-1-(5-methyl-2-(6-methylpyridin-2-yl)benzoyl)piperidin-2-yl)methyl)carbamate

HRID 61026Notes

Reaction equation

HRID 61026 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[N:12]=2)=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[CH3:18][C@@H:19]1[CH2:24][CH2:23][CH2:22][NH:21][C@@H:20]1[CH2:25][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30].CCN(C(C)C)C(C)C.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>C(Cl)Cl>[CH3:18][C@@H:19]1[CH2:24][CH2:23][CH2:22][N:21]([C:7](=[O:9])[C:6]2[CH:10]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]=2[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[N:12]=2)[C@@H:20]1[CH2:25][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 89748212tert-butyl (((2S,3R)-3-methylpiperidin-2-yl)methyl)carbamateHCID 117727727HCID 117727727, compound

Product 1

HCID 117731463tert-Butyl (((2S,3R)-3-methyl-1-(5-methyl-2-(6-methylpyridin-2-yl)benzoyl)piperidin-2-yl)methyl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To the mixture of 5-methyl-2-(6-methylpyridin-2-yl)benzoic acid (0.229 g, 0.868 mmol), tert-butyl (((2S,3R)-3-methylpiperidin-2-yl)methyl)carbamate (0.24 g, 1.04 mmol) and DIPEA (0.3 mL, 1.738 mmol) in DCM (20 mL) was slowly added O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU; 0.278 g, 0.869 mmol). The mixture was stirred at rt for 1 h. The mixture was diluted with DCM and was washed with satd. aq. NaHCO3 and brine and dried over Na2SO4. The solvent was removed in vacuo to obtain the title compound which was used without further purification. ESI-MS (m/z): 438 [M+1]+.

Workup

  1. washwas washed with satd
  2. dry with materialaq. NaHCO3 and brine and dried over Na2SO4
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-1776730848ed49cfb9f2e6a2fcf96798
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

Loading…