1-Hydroxybenzotriazole → HCID 15435307, compound

HRID 617652Notes

Reaction equation

HRID 617652 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13](=[O:29])[N:14]([CH2:25][C:26](O)=[O:27])[CH:15]=[C:16]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:30][CH:31]([CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH:32]([OH:37])[C:33]([F:36])([F:35])[F:34].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13](=[O:29])[N:14]([CH2:25][C:26]([NH:30][CH:31]([CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:32]([OH:37])[C:33]([F:34])([F:35])[F:36])=[O:27])[CH:15]=[C:16]([CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13](=[O:29])[N:14]([CH2:25][C:26]([NH:30][CH:31]([CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:32](=[O:37])[C:33]([F:35])([F:36])[F:34])=[O:27])[CH:15]=[C:16]([CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11741222HCID 11741222, compoundHCID 145032493-Amino-1,1,1-trifluoro-4-phenylbutan-2-ol

Product 2

HCID 15435307HCID 15435307, compoundHCID 21851370HCID 21851370, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(3-Benzyloxycarbonylamino-5-benzyl-2-oxo-1,2-dihydro-1-pyridyl)-N-(1-benzyl-3,3,3-trifluoro-2-hydroxypropyl)acetamide was synthesized in the same manner as in Example 1. That is, 2-(3-benzyloxycarbonylamino-5-benzyl-2-oxo-1,2-dihydro-1-pyridyl)acetic acid (title compound in Reference Example 7, 380 mg, 0.968 mmol) was treated with 3-amino-1,1,1-trifluoro-4-phenyl-2-butanol (title compound in Reference Example 1, 249 mg, 1.14 mmol), WSCI hydrochloride (277 mg, 1.45 mmol) and HOBT (158 mg, 1.17 mmol) in DMF (10 mL) to give 428 mg (74%) of the target compound as a slightly yellow solid.

Sources & evidence

ORD record
ord-f8e5d6318fea4dddb228265e350d27c7
Source dataset
uspto-grants-1999_09
Patent number
US05948785

Reaction notes

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