1-Hydroxybenzotriazole → HCID 86591608, compound

HRID 724528Notes

Reaction equation

HRID 724528 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][NH:10][C:11]([C:13]1[N:14]([CH2:33][CH:34]([CH3:36])[CH3:35])[CH:15]=[C:16]([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:17]=1)=[O:12])(C)(C)C.C(OC(=O)NCCNC(C1[NH:51][C:52]2[C:57]([CH:58]=1)=CC=C(N)C=2)=O)(C)(C)C.C([O:65]C(NCCC(O)=O)=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.C(O)(C(F)(F)F)=O.C1(OC)C=CC=CC=1>CN(C=O)C>[NH2:7][CH2:8][CH2:9][NH:10][C:11]([C:13]1[N:14]([CH2:33][CH:34]([CH3:36])[CH3:35])[CH:15]=[C:16]([NH:18][C:19]([C:21]2[NH:22][C:23]3[C:24]([CH:29]=2)=[CH:25][C:26]([NH:30][C:58](=[O:65])[CH2:57][CH2:52][NH2:51])=[CH:27][CH:28]=3)=[O:20])[CH:17]=1)=[O:12]

Participants

9

Reactant 7

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 66633105Anisole trifluoroacetic acidHCID 69528719{2-[(6-Amino-1H-indole-2-carbonyl)-amino]-ethyl}-carbamic acid tert-butyl esterHCID 69599322HCID 69599322, compound

Product 1

HCID 86591608HCID 86591608, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 116 was reduced by hydrogenation according to the procedure for compound 36, and then reacted with 3-tert-butoxycarbonylaminopropionic acid in DMF in the presence of HBTU, HOBt, and DIEA, followed by deprotection with TFA/anisole according to the procedure for 108. Compound 117 was obtained in 96% yield. MS: 227.62 (M/2+H+).

Sources & evidence

ORD record
ord-478283a7caf24ead86e576830823a8aa
Source dataset
uspto-grants-2006_11
Patent number
US07141680B2

Reaction notes

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