Triethylamine → HCID 11454169, compound

HRID 1866492Notes

Reaction equation

HRID 1866492 reaction equation
[OH:1][C@H:2]([C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([CH2:24][OH:25])[CH:18]=1)[CH2:3][NH:4][C@H:5]([CH3:16])[CH2:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=O.C(N(CC)CC)C.[Cl:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38][NH2:39])=[CH:36][CH:35]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[NH3:4].[Cl:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38][NH:39][C:10](=[O:12])[C:9]2[CH:13]=[CH:14][CH:15]=[C:7]([CH2:6][C@H:5]([NH:4][CH2:3][C@H:2]([OH:1])[C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([CH2:24][OH:25])[CH:18]=3)[CH3:16])[CH:8]=2)=[CH:36][CH:35]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 660364-ChlorobenzylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57978199HCID 57978199, compound

Product 2

HCID 222AmmoniaHCID 11454169HCID 11454169, compoundYield 153.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-[(2R)-2-({(2R)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)propyl]benzoic acid (Preparation 59) (120 mg, 0.27 mmol) in DMF (3 ml) was added triethylamine (111 μl, 0.79 mmol), 4-chlorobenzylamine (39 μl, 0.32 mmol), and HBTU (110 mg, 0.29 mmol) and the resulting solution stirred at room temperature for 18 hours. The solvent was removed in vacuo and the residue purified by flash column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (93:7:0.7 changing to 90:10:1, by volume) to give the title compound as a white foam (97 mg). 1H NMR (400 MHz, CD3OD): δ=7.70-7.68 (1H, d), 7.66 (1H, s), 7.38-7.30 (6H, m), 7.23 (1H, d), 7.05-7.03 (1H, dd), 6.70-6.68 (1H, d), 4.67-4.64 (1H, dd), 4.62 (2H, s), 4.55 (2H, s), 3.15-3.07 (1H, m), 3.00-2.86 (2H, m), 2.82-2.78 (1H, dd), 2.72-2.67 (1H, dd), 1.13-1.12 (3H, d) ppm. LRMS (electrospray): m/z [M+H]+ 469, [M+Na]+ 491, [M−H]− 467.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue purified by flash column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-ab5306f1926c4e7f9f09d97315682ca4
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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