Piperidine → (S)-2-amino-6-((2-tert-butoxy-2-oxoethyl)(thiazol-2-ylmethyl)amino)hexanoic acid

HRID 56316Notes

Reaction equation

HRID 56316 reaction equation
N1CCCCC1.C1C2C(COC(=O)[NH:23][C@H:24]([C:44]([OH:46])=[O:45])[CH2:25][CH2:26][CH2:27][CH2:28][N:29]([CH2:38][C:39]3[S:40][CH:41]=[CH:42][N:43]=3)[CH2:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])C3C(=CC=CC=3)C=2C=CC=1>CN(C=O)C>[NH2:23][C@@H:24]([CH2:25][CH2:26][CH2:27][CH2:28][N:29]([CH2:30][C:31]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:37])[CH2:38][C:39]1[S:40][CH:41]=[CH:42][N:43]=1)[C:44]([OH:46])=[O:45]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 59408631(S)-1-(9H-fluoren-9-yl)-14,14-dimethyl-3,12-dioxo-10-(thiazol-2-ylmethyl)-2,13-dioxa-4,10-diazapentadecane-5-carboxylic acid

Product 1

HCID 59408640(S)-2-amino-6-((2-tert-butoxy-2-oxoethyl)(thiazol-2-ylmethyl)amino)hexanoic acidYield 55.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Piperidine (0.20 mL) was added to a solution of (S)-1-(9H-fluoren-9-yl)-14,14-dimethyl-3,12-dioxo-10-(thiazol-2-ylmethyl)-2,13-dioxa-4,10-diazapentadecane-5-carboxylic acid (72.5 mg, 0.125 mmol) in DMF (1.0 mL). The mixture was stirred at room temperature for 2 hrs. Solvent was evaporated under reduce pressure to afford a residue, which was purified by flash chromatography over silica gel to afford (S)-2-amino-6-((2-tert-butoxy-2-oxoethyl)(thiazol-2-ylmethyl)amino)hexanoic acid (25 mg, 35%). 1H NMR (400 MHz, CD3OD) 7.70 (d, J=3.6 Hz, 1H), 7.53 (d, J=3.2 Hz, 1H), 4.15 (s, 2H), 3.52 (dd, J=7.2, 5.2 Hz, 1H), 3.38 (s, 2H), 2.73 (t, J=7.2 Hz, 2H), 1.91-1.76 (m, 2H), 1.60-1.44 (m, 13H); MS (ESI), 358 (M+H)+.

Workup

  1. customSolvent was evaporated
  2. customto afford a residue, which
  3. customwas purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-7c5192676b95446f962c42082fd96c3b
Source dataset
uspto-grants-2016_09
Patent number
US09433594B2

Reaction notes

Loading…