Diisopropylethylamine → (S)-2-[4-(5-Methoxycarbonyl-furan-2-yl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester

HRID 737189Notes

Reaction equation

HRID 737189 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16](=[O:35])[NH:17][C:18]1[S:19][C:20](C2C=CC=C(C(=O)NC3CC3)C=2)=[CH:21][N:22]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:36][O:37][C:38]([C:40]1[O:41][C:42](C2N=C(N)SC=2)=[CH:43][CH:44]=1)=[O:39].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(OC(N1CCC[C@H]1C(O)=O)=O)C1C=CC=CC=1>>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16](=[O:35])[NH:17][C:18]1[S:19][CH:20]=[C:21]([C:42]2[O:41][C:40]([C:38]([O:37][CH3:36])=[O:39])=[CH:44][CH:43]=2)[N:22]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 81531DiisopropylethylamineHCID 101987Benzyloxycarbonyl-L-prolineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57849886(S)-2-[5-(3-Cyclopropylcarbamoyl-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl esterHCID 866164355-(2-Amino-thiazol-4-yl)-furan-2-carboxylic acid methyl ester

Product 1

HCID 86616436(S)-2-[4-(5-Methoxycarbonyl-furan-2-yl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester

Procedure

In a similar procedure as described for the synthesis of Compound 5312 (Example 312), 5-(2-amino-thiazol-4-yl)-furan-2-carboxylic acid methyl ester was treated with HATU (0.98 g, 2.38 mmol), DIEA (0.7 mL, 5.36 mmol), and (S)-Pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester (0.61 g, 2.45 mmol) to furnish (S)-2-[4-(5-Methoxycarbonyl-furan-2-yl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester; MS: 169.1 (M+H+).

Sources & evidence

ORD record
ord-c739cfe4c73b4a328536cab42abd9c0f
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

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