Diisopropylethylamine → N-[N-(2-Heptenoyl)-3,5-difluoro-L-phenylalanyl]cyclo(Ser*-Pro-L-Pip-Ala-4beta-methyl-Pro-)

HRID 751768

Reaction equation

HRID 751768 reaction equation
FC(F)(F)C([O-])=O.[F:8][C:9]1[CH:10]=[C:11]([CH2:16][C@H:17]([NH3+:54])[C:18](=[O:53])[NH:19][C@H:20]2[CH2:45][O:44][C:43](=[O:46])[C@H:42]3[N:38]([CH2:39][C@H:40]([CH3:47])[CH2:41]3)[C:37](=[O:48])[C@H:36]([CH3:49])[NH:35][C:34](=[O:50])[C@H:33]3[N:28]([CH2:29][CH2:30][CH2:31][CH2:32]3)[C:27](=[O:51])[C@H:26]3[N:22]([CH2:23][CH2:24][CH2:25]3)[C:21]2=[O:52])[CH:12]=[C:13]([F:15])[CH:14]=1.[C:55](O)(=[O:62])/[CH:56]=[CH:57]/[CH2:58][CH2:59][CH2:60][CH3:61].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)C(C)C)C>C(#N)C.O.CN(C)C=O>[F:15][C:13]1[CH:12]=[C:11]([CH2:16][C@H:17]([NH:54][C:55](=[O:62])/[CH:56]=[CH:57]/[CH2:58][CH2:59][CH2:60][CH3:61])[C:18](=[O:53])[NH:19][C@H:20]2[CH2:45][O:44][C:43](=[O:46])[C@H:42]3[N:38]([CH2:39][C@H:40]([CH3:47])[CH2:41]3)[C:37](=[O:48])[C@H:36]([CH3:49])[NH:35][C:34](=[O:50])[C@H:33]3[N:28]([CH2:29][CH2:30][CH2:31][CH2:32]3)[C:27](=[O:51])[C@H:26]3[N:22]([CH2:23][CH2:24][CH2:25]3)[C:21]2=[O:52])[CH:10]=[C:9]([F:8])[CH:14]=1

Participants

7

Reactant 4

HCID 81531Diisopropylethylamine2×HCID 52827092-Heptenoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86598033(S)-2-(3,5-Difluorophenyl)-1-((3S,9S,13S,15R,19S,22S)-15, 19-Dimethyl-2,8,12,18,21-pentaoxo-11-oxa-1,7,17,20-tetraaza-tetracyclo[20.4.0.03,7.013,17]hexacos-9-ylcarbamoyl)-ethylammonium 2,2,2-trifluoroacetate

Product 1

HCID 11679386N-[N-(2-Heptenoyl)-3,5-difluoro-L-phenylalanyl]cyclo(Ser*-Pro-L-Pip-Ala-4beta-methyl-Pro-)

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

101.5 mg (0.13 mmol) of the compound from example 29A and 23.0 mg (0.17 mmol) of trans-2-heptenoic acid are introduced under argon into anhydrous dimethylformamide (2 ml) at 0° C. and then 65.0 mg (0.17 mmol) of HATU and 0.025 ml (0.14 mmol) of ethyldiisopropylamine are added. After 30 min, a further 0.05 ml (0.29 mmol) of ethyldiisopropylamine are added to the reaction mixture. The reaction mixture is stirred overnight with slow warming to RT. The reaction solution is subjected directly to an RP-HPLC using acetonitrile/water as eluent. In the course of this, 63 mg (62% of th.) of a colorless solid are obtained.

Workup

  1. customIn the course of this, 63 mg (62% of th.) of a colorless solid are obtained

Sources & evidence

ORD record
ord-7124a5e3e5414e6c9a84f8113aefb998
Source dataset
uspto-grants-2008_07
Patent number
US07405201B2

Linked notes

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