1-Hydroxybenzotriazole → HCID 59784092, compound

HRID 2079762Notes

Reaction equation

HRID 2079762 reaction equation
[NH2:1][C@@H:2]([CH:34]([CH3:36])[CH3:35])[C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7][C@H:6]1[C:21]([NH:23][C@H:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27][CH2:26][CH2:25]1)=[O:22])=[O:4].[C:37]([N:44]([CH3:50])[C@H:45]([C:47](O)=[O:48])[CH3:46])([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38].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.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[C:40]([O:39][C:37]([N:44]([CH3:50])[C@@H:45]([CH3:46])[C:47]([NH:1][C@@H:2]([CH:34]([CH3:36])[CH3:35])[C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7][C@H:6]1[C:21]([NH:23][C@H:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27][CH2:26][CH2:25]1)=[O:22])=[O:4])=[O:48])=[O:38])([CH3:43])([CH3:42])[CH3:41]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 7009590(2S)-2-(((tert-butoxy)carbonyl)(methyl)amino)propanoic acidHCID 59784095HCID 59784095, compound

Product 1

HCID 59784092HCID 59784092, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Amine 5 (12.57 g, 25.5 mmol) is then coupled with BOC-N-methyl-L-alanine (5.18 g, 25.5 mmol) using DIEA (22.3 mL, 0.13 mol), HBTU (10.64 g, 28.1 mmol) and HOBt (3.79 g, 28.1 mmol) in DMF (550 mL) under the same conditions as in step 1 above. Purification is carried out by flash chromatography on silica gel (CH2Cl2 as eluent initially, followed by 50% Et2O/CH2Cl2 to elute the desired product). The desired coupled product 6 is isolated as a white foam (15.30 g, 89% yield): 1H NMR δ (CDCl3) 7.28-7.38 (br m, 5H), 7.03-7.19 (br m, 4H), 6.73 (br s, 1H), 6.02-6.35 (br m, 1H), 5.05-5.26 (br m, 4H), 3.84-4.82 (br m, 5H), 2.68-3.56 (br m, 9H), 1.70-2.07 (br m, 5H), 1.47 (s, 9H), 0.60-1.33 (br m, 8H); LCMS (APCl+) 679.0 (MH+), 579.0 (MH+-BOC, 100%); HPLC(C18 column) 99.4%.

Workup

  1. customPurification
  2. washto elute the desired product)

Sources & evidence

ORD record
ord-4a8704297203435785814dcbf67a79cd
Source dataset
uspto-grants-2011_04
Patent number
US07932255B2

Reaction notes

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