HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Piperidine → A 410099.1, amine-Boc

HRID 1481915
Notes
Print preview

Reaction equation

HRID 1481915 reaction equation
C1C2C(COC(=O)[NH:17][C@H:18]3[CH2:22][C@@H:21]([C:23](=[O:35])[NH:24][C@H:25]4[C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[CH2:28][CH2:27][CH2:26]4)[N:20]([C:36](=[O:58])[C@@H:37]([NH:44][C:45](=[O:57])[C@@H:46]([N:48]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[CH3:49])[CH3:47])[CH:38]4[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]4)[CH2:19]3)C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>CN(C=O)C>[C:53]([O:52][C:50](=[O:51])[N:48]([C@H:46]([C:45](=[O:57])[NH:44][C@@H:37]([CH:38]1[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]1)[C:36]([N:20]1[CH2:19][C@@H:18]([NH2:17])[CH2:22][C@H:21]1[C:23](=[O:35])[NH:24][C@H:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:28][CH2:27][CH2:26]1)=[O:58])[CH3:47])[CH3:49])([CH3:54])([CH3:55])[CH3:56]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 8082PiperidineHCID 90220982{(3S,5S)-1-{(S)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-propionylamino]-2-cyclohexyl-acetyl}-5-[(R)-(1,2,3,4-tetrahydro-naphthalen-1-yl)carbamoyl]-pyrrolidin-3-yl}-carbamic acid 9H-fluoren-9-ylmethyl ester2×

Product 1

HCID 90221030A 410099.1, amine-BocYield 78.3%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

{(3S,5S)-1-{(S)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-propionylamino]-2-cyclohexyl-acetyl}-5-[(R)-(1,2,3,4-tetrahydro-naphthalen-1-yl)carbamoyl]-pyrrolidin-3-yl}-carbamic acid 9H-fluoren-9-ylmethyl ester (Intermediate 25) (100 mg, 124 μM) was dissolved in DMF (0.9 mL) at room temperature and piperidine (0.1 mL) was added. The mixture was stirred at room temperature for 30 minutes, concentrated and the residue purified by chromatography over silica gel to give the title compound as white foam (56.7 mg, 78%). LC-MS: 585 (M+H).

Workup

  1. concentrationconcentrated
  2. customthe residue purified by chromatography over silica gel

Sources & evidence

ORD record
ord-4888481ace334aa7aead122dc6d5bdde
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09409888B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes