1-Hydroxybenzotriazole → HCID 86591606, compound

HRID 724526Notes

Reaction equation

HRID 724526 reaction equation
[C:1]([CH2:4][CH2:5][NH:6][C:7]([C:9]1[N:13]([CH2:14][CH:15]([CH3:17])[CH3:16])[CH:12]=[C:11]([NH:18][C:19]([C:21]2[NH:22][C:23]3[C:28]([CH:29]=2)=[CH:27][C:26]([N+:30]([O-])=O)=[CH:25][CH:24]=3)=[O:20])[CH:10]=1)=[O:8])(=[NH:3])[NH2:2].C(OC([NH:40][CH2:41][CH2:42][C:43](O)=[O:44])=O)(C)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[C:1]([CH2:4][CH2:5][NH:6][C:7]([C:9]1[N:13]([CH2:14][CH:15]([CH3:17])[CH3:16])[CH:12]=[C:11]([NH:18][C:19]([C:21]2[NH:22][C:23]3[C:28]([CH:29]=2)=[CH:27][C:26]([NH:30][C:43](=[O:44])[CH2:42][CH2:41][NH2:40])=[CH:25][CH:24]=3)=[O:20])[CH:10]=1)=[O:8])(=[NH:3])[NH2:2]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86591607HCID 86591607, compound

Product 1

HCID 86591606HCID 86591606, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 113 was reduced to its amine by hydrogenation according to the procedure for 36. The amine was then reacted with 3-tert-butoxycarbonylaminopropionic acid in the presence of HBTU, HOBt, and DIEA in dry DMF, followed by de-Boc protection according to the procedure for 109 to give 114 in quantitative yield. MS: 241.15 (M/2+H+).

Sources & evidence

ORD record
ord-27391a4e2ad64b7bbdd2f86e80507f44
Source dataset
uspto-grants-2006_11
Patent number
US07141680B2

Reaction notes

Loading…