1-Hydroxybenzotriazole → HCID 178454183, compound

HRID 519414Notes

Reaction equation

HRID 519414 reaction equation
[NH:1]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C@H:2]([C:10]([NH:12][C@H:13]([C:24]([OH:26])=[O:25])[CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8].Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[NH:1]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C@H:2]([C:10]([NH:12][C@H:13]([C:24]([OH:26])=[O:25])[CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:8])[NH2:9]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178454186HCID 178454186, compound

Product 1

HCID 178454183HCID 178454183, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of Boc-L-Arg-L-Trp-OH hydrochloride (100 mg, 0.20 mmoles), H-D-Arg-D-Trp-OBzl di-p-toluenesulphonic acid (175 mg, 0.21 mmoles), HOBt (110 mg, 0.72 mmoles) and DIPEA (164 μl, 0.96 mmoles) in DMF (2 ml) cooled on ice was added HBTU (91 mg, 0.24 mmoles) in small portions over 10 minutes. The mixture was stirred on ice for 3 hours and workup performed as described for KP-3-2. After workup, the organic layer contained only minor amounts of the desired product as judged by analytical RP-HPLC. The pooled water phases was extracted with 3×15 ml ethyl acetete and evaporated to afford the crude product.

Sources & evidence

ORD record
ord-80e6bf08bce9451a9ae945bdfd4d16fb
Source dataset
uspto-grants-2015_08
Patent number
US09115169B2

Reaction notes

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