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Diisopropylethylamine → Tert-Butyl 4-(3-(Tert-Butyldisulfanyl)-2-(Isobutoxycarbonylamino)Propanamido)Piperidine-1-Carboxylate

HRID 923720
Notes
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Reaction equation

HRID 923720 reaction equation
[C:1]([S:5][S:6][CH2:7][CH:8]([NH:12][C:13]([O:15][CH2:16][CH:17]([CH3:19])[CH3:18])=[O:14])[C:9]([OH:11])=O)([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[C:53]([N:60]1[CH2:65][CH2:64][CH:63]([NH2:66])[CH2:62][CH2:61]1)([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54]>CN(C=O)C>[C:1]([S:5][S:6][CH2:7][CH:8]([NH:12][C:13]([O:15][CH2:16][CH:17]([CH3:19])[CH3:18])=[O:14])[C:9]([NH:66][CH:63]1[CH2:62][CH2:61][N:60]([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[CH2:65][CH2:64]1)=[O:11])([CH3:2])([CH3:3])[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 871033123-(Tert-Butyldisulfanyl)-2-(Isobutoxycarbonylamino)Propanoic Acid

Product 1

HCID 87107224
Tert-Butyl 4-(3-(Tert-Butyldisulfanyl)-2-(Isobutoxycarbonylamino)Propanamido)Piperidine-1-Carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the acid from Example 59 (6.98 g, 22.6 mmol) in DMF (50 ml was added HATU (8.58 g, 22.6 mmol). After 30 min, Hunig base (4.71 ml, 27.1 mmol) and 1-Boc-4-amino piperidine (5.43 g, 27.1 mmol) were added to the mixture. The reaction was continued stirring at RT for another 3 h. DMF was removed at high vacuum, the crude residue was dissolved in EtAc (300 ml), washed with H2O (50 ml×3). The title compound was obtained after ISCO purification (5% MeOH/DCM).

Workup

  1. customDMF was removed at high vacuum
  2. dissolutionthe crude residue was dissolved in EtAc (300 ml)
  3. washwashed with H2O (50 ml×3)

Sources & evidence

ORD record
ord-42028ecd482a4a6fa8304391e0a2b61f
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09278987B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes