Diisopropylethylamine → (S)-2-[[1-(4-azidobutyl)cyclopentanecarbony]amino]-3-[4-(1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)phenyl]propionic acid propyl ester

HRID 63735Notes

Reaction equation

HRID 63735 reaction equation
[CH2:1]([O:4][C:5](=[O:26])[C@@H:6]([NH2:25])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:15](=[O:24])[N:16]([CH3:23])[C:17](=[O:22])[N:18]([CH3:21])[C:19]=2[CH3:20])=[CH:10][CH:9]=1)[CH2:2][CH3:3].[N:27]([CH2:30][CH2:31][CH2:32][CH2:33][C:34]1([C:39](O)=[O:40])[CH2:38][CH2:37][CH2:36][CH2:35]1)=[N+:28]=[N-:29].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>>[CH2:1]([O:4][C:5](=[O:26])[C@@H:6]([NH:25][C:39]([C:34]1([CH2:33][CH2:32][CH2:31][CH2:30][N:27]=[N+:28]=[N-:29])[CH2:38][CH2:37][CH2:36][CH2:35]1)=[O:40])[CH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[C:15](=[O:24])[N:16]([CH3:23])[C:17](=[O:22])[N:18]([CH3:21])[C:19]=2[CH3:20])=[CH:12][CH:13]=1)[CH2:2][CH3:3]

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 226601411-(4-Azidobutyl)cyclopentanecarboxylic acidHCID 86691352(S)-2-amino-3-[4-(1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)phenyl]propionic acid propyl ester

Product 1

HCID 89720754(S)-2-[[1-(4-azidobutyl)cyclopentanecarbony]amino]-3-[4-(1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)phenyl]propionic acid propyl ester

Procedure

The title compound was prepared using a similar procedure as described in Example 1, Step 8, starting from (S)-2-amino-3-[4-(1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)phenyl]propionic acid propyl ester (10.78 g, 30 mmol), 1-[4-azidobutyl]cyclopentanecarboxylic acid (8.24 g, 39 mmol), HBTU (14.79 g, 39 mmol), and DIPEA (11.63 g, 15.68 mL, 90 mmol), and after ISCO column chromatography purification, resulted in an amorphous off-white solid (14.1 g, 85%). ES(+)-HRMS m/e calcd. for C29H40N6O5 (M+H)+ 553.3133, obsd. 553.3133.

Workup

  1. customafter ISCO column chromatography purification

Sources & evidence

ORD record
ord-f7989408f3af4032a0c63967aca3019f
Source dataset
uspto-grants-2016_09
Patent number
US09447035B2

Reaction notes

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