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Diisopropylethylamine → HCID 58360481, compound

HRID 2040019
Notes
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Reaction equation

HRID 2040019 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:10]([NH:12][C@@H:13]([CH:21]([CH3:23])[CH3:22])[CH2:14][O:15][CH2:16][CH2:17][C:18]([OH:20])=O)=[O:11])=[CH:4][CH:3]=1.C1C=NC2N(O)N=NC=2C=1.C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(Cl)Cl>[CH:21]([C@@H:13]1[NH:12][C:10](=[O:11])[C@H:9]([NH:24][C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:31])[CH3:30])[CH2:8][C:5]2=[CH:6][CH:7]=[C:2]([CH:3]=[CH:4]2)[NH:1][C:18](=[O:20])[CH2:17][CH2:16][O:15][CH2:14]1)([CH3:22])[CH3:23]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58360480HCID 58360480, compound

Product 1

HCID 58360481HCID 58360481, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

The 3-{(S)-2-[(R)-3-(4-aminophenyl)-2-tert-butoxycarbonylaminopropionylamino]-3-methylbutoxy}propionic acid (˜225 mg) obtained as crude product in 7-1 D was dissolved in 225 ml of DMF. 70.0 mg (0.51 mmol) of HOAt, 0.26 ml (1.5 mmol) of N,N-diisopropylethylamine and 195.4 mg (0.51 mmol) of HATU were successively added to this solution, and the mixture was stirred at room temp. for 1 h. The reaction mixture was concentrated in vacuo. The residue obtained in this way was taken up in CH2Cl2, washed with sat. NaHCO3 solution, dried over MgSO4 and freed of solvent in vacuo. The ring-closed compound obtained in this way was employed crude in the next stage. Yield: 215.0 mg.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue obtained in this way
  3. washwashed with sat. NaHCO3 solution
  4. dry with materialdried over MgSO4
  5. customThe ring-closed compound obtained in this way

Sources & evidence

ORD record
ord-02563ca644ae4f879ae48ab7bcbc04e1
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08580777B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes