Diisopropylethylamine → HCID 58865748, compound

HRID 1354866Notes

Reaction equation

HRID 1354866 reaction equation
[CH2:1]([O:8][C:9]1[N:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C.[CH:51]1[C:63]2[CH:62]([CH2:64][O:65][C:66](=[O:83])[NH:67][C:68]3[CH:73]=[CH:72][C:71]([NH2:74])=[C:70]([O:75][CH2:76][C:77]4[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=4)[CH:69]=3)[C:61]3[C:56](=[CH:57][CH:58]=[CH:59][CH:60]=3)[C:55]=2[CH:54]=[CH:53][CH:52]=1>CN(C=O)C.CCOC(C)=O>[CH:51]1[C:63]2[CH:62]([CH2:64][O:65][C:66](=[O:83])[NH:67][C:68]3[CH:73]=[CH:72][C:71]([NH:74][C:11]([C:10]4[C:9]([O:8][CH2:1][C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=5)=[N:17][CH:16]=[CH:15][CH:14]=4)=[O:13])=[C:70]([O:75][CH2:76][C:77]4[CH:78]=[CH:79][CH:80]=[CH:81][CH:82]=4)[CH:69]=3)[C:61]3[C:56](=[CH:57][CH:58]=[CH:59][CH:60]=3)[C:55]=2[CH:54]=[CH:53][CH:52]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 7626622-Benzyloxy-nicotinic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58865047(4-Amino-3-benzyloxyphenyl)-carbamic acid 9H-fluoren-9-ylmethyl ester

Product 1

HCID 58865748HCID 58865748, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Benzyloxy-nicotinic acid (423) (0.157 g, 0.687 mmol) was dissolved in DMF (4 mL), 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyl-uronium hexafluorophosphate (HBTU) (0.273 g, 0.721 mmol) was added followed by iPr2EtN (0.143 mL, 0.824 mmol) and the mixture was shaken in a Teflon septum capped 40 mL vial at room temperature for 25 minutes. (4-Amino-3-benzyloxy-phenyl)-carbamic acid 9H-fluoren-9-ylmethyl ester (65) (0.3 g, 0.687 mmol) was added and the mixture was shaken at room temperature for 16 h. LC-MS indicated complete coupling at this point. The mixture was diluted with EtOAc (25 mL), washed with water (15 mL), NaHCO3 (aqueous saturated, 15 mL) and brine (15 mL) via extraction, dried over MgSO4 and concentrated to give a brown oil. Purification by flash chromatography (eluding with 15–100% EtOAc/hexane in 30 minutes) gave the desired product (424) as a yellow powder upon concentration (0.436 g, 0.673 mmol, 98% yield). LC-MS (ESI): (exact mass: 647.24) m/e=648.3 [M+1]+ (100%).

Workup

  1. customcapped 40 mL vial at room temperature for 25 minutes
  2. washwashed with water (15 mL), NaHCO3 (aqueous saturated, 15 mL) and brine (15 mL) via extraction
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customto give a brown oil
  6. customPurification by flash chromatography (eluding with 15–100% EtOAc/hexane in 30 minutes)

Sources & evidence

ORD record
ord-49e6cfd2058740bebd4ab5f302f64f3f
Source dataset
uspto-grants-2007_05
Patent number
US07223759B2

Reaction notes

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