Hydrochloric Acid → HCID 87735364, compound

HRID 902952Notes

Reaction equation

HRID 902952 reaction equation
[C:1]([O:5][C:6](=[O:32])[CH2:7][CH:8]([CH2:12][CH2:13][P:14]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C:9]([OH:11])=O)([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[C:42]1([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH:47]=[CH:46][C:45]([CH2:48][CH2:49][NH2:50])=[CH:44][CH:43]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.Cl>CN(C=O)C>[C:1]([O:5][C:6](=[O:32])[CH2:7][CH:8]([C:9](=[O:11])[NH:50][CH2:49][CH2:48][C:45]1[CH:46]=[CH:47][C:42]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)=[CH:43][CH:44]=1)[CH2:12][CH2:13][P:14]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])([CH3:3])([CH3:2])[CH3:4]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 282102-(4-Biphenyl)ethylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 87735465HCID 87735465, compound

Product 1

HCID 87735364HCID 87735364, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the compound of Example 77 (770 mg, 1.67 mmol) in anhydrous DMF (2 mL) was treated with DIEA (1.5 mL), 4-biphenylethyl amine (672 mg, 3.34 mmol), and TBTU (775 mg, 2.34 mmol). The reaction mixture was stirred for 24 h at room temperature after which HCl (1M, excess) was added. The mixture was extracted several times with ethyl acetate. The recombined organic layer was washed with brine, dried over sodium sulfate, filtered and evaporated. The residue was flashed with 50% ethyl acetate in hexanes and the desired product was obtained as a white solid. 1H NMR (CDCl3, 400 MHz: 1.41(s, 9H); 1.61-1.87(m, 4H); 2.15, 2.59(2dd, J1=16.4 Hz. J2=4.2 Hz, 2H); 2.67(m, 1H); 2.80(m, 2H); 3.49(m, 2H); 4.96(m, 4H); 6.35(t, J=5.6 Hz); 7.32(m, 13H); 7.42(m, 2H); 7.55(m, 4H); 31P NMR(CDCl3, 400 MHz): 33.05.

Workup

  1. additionwas added
  2. extractionThe mixture was extracted several times with ethyl acetate
  3. washThe recombined organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-29950f6169894712b802f3db0588705f
Source dataset
uspto-grants-2008_04
Patent number
US07365091B2

Reaction notes

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