N-(tert-butoxycarbonyl)glycine → (1-(2-(Tert-butoxycarbonyl)aminoacetyl)-4-(2-chlorobenzylcarbamoyl)piperidin-4-yl)methyl 4-ethylphenylcarbamate

HRID 655950Notes

Reaction equation

HRID 655950 reaction equation
[NH:1]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:2][C:3]([OH:5])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[CH2:38]([C:40]1[CH:45]=[CH:44][C:43]([NH:46][C:47](=[O:67])[O:48][CH2:49][C:50]2([C:56](=[O:66])[NH:57][CH2:58][C:59]3[CH:64]=[CH:63][CH:62]=[CH:61][C:60]=3[Cl:65])[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]2)=[CH:42][CH:41]=1)[CH3:39].CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:38]([C:40]1[CH:45]=[CH:44][C:43]([NH:46][C:47](=[O:67])[O:48][CH2:49][C:50]2([C:56](=[O:66])[NH:57][CH2:58][C:59]3[CH:64]=[CH:63][CH:62]=[CH:61][C:60]=3[Cl:65])[CH2:55][CH2:54][N:53]([C:3](=[O:5])[CH2:2][NH:1][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:52][CH2:51]2)=[CH:42][CH:41]=1)[CH3:39]

Participants

6

Reactant 4

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69162882(4-(2-Chlorobenzylcarbamoyl)piperidin-4-yl)methyl 4-ethylphenylcarbamate hydrochloride

Product 1

HCID 59778528(1-(2-(Tert-butoxycarbonyl)aminoacetyl)-4-(2-chlorobenzylcarbamoyl)piperidin-4-yl)methyl 4-ethylphenylcarbamateYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Boc-Gly-OH (54 mg, 0.31 mmol, 1.2 equiv.) in DMF (1 mL) were added HATU (120 mg, 0.31 mmol, 1.2 equiv.), followed by addition of (4-(2-chlorobenzylcarbamoyl)piperidin-4-yl)methyl 4-ethylphenylcarbamate hydrochloride (120 mg, 0.26 mmol, 1 equiv.) and DIEA (89 μL, 0.51 mmol, 2 equiv.) at rt The reaction mixture was stirred for 3 h and purified on RP-HPLC using a mixture of acetonitrile and H2O to give (1-(2-(tert-butoxycarbonyl)aminoacetyl)-4-(2-chlorobenzylcarbamoyl)piperidin-4-yl)methyl 4-ethylphenylcarbamate (127 mg, 84%). LRMS (M-Boc+H+) m/z 487.1.

Workup

  1. custompurified on RP-HPLC
  2. additiona mixture of acetonitrile and H2O

Sources & evidence

ORD record
ord-5d6d17be7e3946719bec7d15ae4fa003
Source dataset
uspto-grants-2011_12
Patent number
US08071625B2

Reaction notes

Loading…