Triethylamine → HCID 11262631, compound

HRID 1174394Notes

Reaction equation

HRID 1174394 reaction equation
[CH3:1][O:2][C:3]([NH:5][CH:6]([NH:10][C:11]([O:13][CH3:14])=[O:12])[C:7]([OH:9])=O)=[O:4].ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.[NH2:36][C@@H:37]([CH2:68][C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1)[C@@H:38]([OH:67])[CH2:39][C@@H:40]([NH:54][C:55]([C@@H:57]([NH:62][C:63](=[O:66])[O:64][CH3:65])[C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56])[CH2:41][C:42]1[CH:47]=[CH:46][C:45]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][N:49]=2)=[CH:44][CH:43]=1.C(N(CC)CC)C>CN(C)C=O>[CH2:68]([C@H:37]([NH:36][C:7](=[O:9])[CH:6]([NH:5][C:3](=[O:4])[O:2][CH3:1])[NH:10][C:11]([O:13][CH3:14])=[O:12])[C@@H:38]([OH:67])[CH2:39][C@@H:40]([NH:54][C:55](=[O:56])[C@H:57]([C:58]([CH3:60])([CH3:61])[CH3:59])[NH:62][C:63]([O:64][CH3:65])=[O:66])[CH2:41][C:42]1[CH:47]=[CH:46][C:45]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][N:49]=2)=[CH:44][CH:43]=1)[C:69]1[CH:70]=[CH:71][CH:72]=[CH:73][CH:74]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 13800747HCID 13800747, compoundHCID 16037867methyl (1S)-1-[({(1S,3S,4S)-4-amino-3-hydroxy-5-phenyl-1-[4-(2-pyridinyl)benzyl]pentyl}amino)carbonyl]-2,2-dimethylpropylcarbamate

Product 1

HCID 11262631HCID 11262631, compoundYield 88.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from Example 169A (13.2 mg, 0.06 mmol) was dissolved in N,N-dimethylformamide (0.25 mL) and N-hydroxybenzotriazole (13 mg, 0.10 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (18.4 mg, 0.10 mmol) were added followed by the product from Example 2C (34.2 mg, 0.06 mmol). Triethylamine (9 uL, 0.06 mmol) was added and the mixture was stirred at ambient temperature for 18 hours. The solution was concentrated and the crude residue was purified on a 2 mm preparative silica gel TLC plate (5% CH3OH/CHCl3) to give an amorphous solid (38.4 mg, 83%). 1H NMR (CDCl1) δ 8.65 (d, 1H), 7.86 (d, 2H), 7.78-7.60 (m, 2H), 7.27-7.11 (m, 9H), 6.94-6.70 (br s, 1H), 6.36-6.24 (br s, 1H), 6.24-6.04 (br d, 1H), 6.02-5.84 (br d, 1H), 5.41-5.25 (m, 2H), 4.23-4.10 (m, 1H), 4.10-3.95 (q, 1H), 3.75 (d, 1H), 3.67 (s, 3H), 3.66 (s, 3H), 3.63 (s, 3H), 2.98-2.8 (m, 3H), 2.8-2.65 (m, 1H), 0.91 (s, 9H).

Workup

  1. concentrationThe solution was concentrated
  2. customthe crude residue was purified on a 2 mm preparative silica gel TLC plate (5% CH3OH/CHCl3)

Sources & evidence

ORD record
ord-9b1cd89e5666477ba147f77179b10298
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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