Diisopropylethylamine → HCID 57463495, compound

HRID 2081118Notes

Reaction equation

C([C@@:3]1([CH:10]=[CH2:11])[CH2:5][C@@:4]1([C:7]([O-:9])=[O:8])[NH2:6])C.[C:12]([O:16][C:17]([N:19]1[CH:28]([C:29]([OH:31])=O)[CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([O:32][C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[CH:34]=3)[CH:25]=2)[CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)[C:51]2N=CC=C[C:50]=2N=N1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH2:50]([O:9][C:7]([C@@:4]1([NH:6][C:29]([CH:28]2[CH2:27][C:26]3[C:21](=[CH:22][CH:23]=[C:24]([O:32][C:33]4[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[CH:34]=4)[CH:25]=3)[CH2:20][N:19]2[C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:18])=[O:31])[CH2:5][C@H:3]1[CH:10]=[CH2:11])=[O:8])[CH3:51]

Participants

Conditions

Temperature: 0 °C

Procedure

To a flask charged with ethyl-(1R,2S)-1-amino-2-vinylcyclopropyl carboxylate (1, 1.0 g, 5.2 mmol), 2-(tert-butoxycarbonyl)-6-(3-chlorophenoxy)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (2.31 g, 1.1 equiv), and O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) (2.7 g, 1.1 equiv) were added 30 mL DMF to make a solution. It was cooled to 0° C. in an ice-water bath, followed by slow addition of a solution of N,N-Diisopropylethylamine (DIEA) (4.4 mL, 4 equiv) in DMF (15 mL) while stirring. The reaction was allowed to warm up to rt and stirred overnight

Workup

temperatureto warm up to rt
stirringstirred overnight

Sources & evidence

ORD record: ord-8e92b6ae21dd4c5c8acc1c18aaf98693
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932277B2

Reaction notes

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