Triethylamine → HCID 57573695, compound

HRID 2427929Notes

Reaction equation

HRID 2427929 reaction equation
C12CC3CC(CC(C3)C1)C2.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2N=N1.[CH3:45][O:46][C:47]1[C:52]([O:53][CH3:54])=[CH:51][C:50]([CH2:55][C:56]([OH:58])=[O:57])=[C:49]([CH2:59][N:60](C2C=CC=CC=2)[C:61]([CH3:63])=[O:62])[CH:48]=1>CN(C=O)C>[CH3:45][O:46][C:47]1[C:52]([O:53][CH3:54])=[CH:51][C:50]([CH2:55][C:56]([OH:58])=[O:57])=[C:49]([CH2:59][NH:60][C:61](=[O:62])[CH2:63][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:48]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9238AdamantaneHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 67148381HCID 67148381, compound

Product 1

HCID 57573695HCID 57573695, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-[1-(3-Hydroxy)phenyl)-1-methoxymethylene]tricyclo[3.3.1.13,7]decane 3a (520 mg), triethylamine (800 μl) and benzotriazol-1-yloxytris(dimethylamino)-phosphonium hexafluorophosphate (BOP) (950 mg) were added to a solution of 4,5-dimethoxy-2-[(phenylacetamino)methyl]phenylacetic acid 7 (656 mg, 1.91 mmol) in anhydrous DMF (10 ml). The reaction mixture was stirred at ambient temperature for 6 hours. The mixture was concentrated under vacuum. Chromatography on silica gel using cyclohexane/EtOAc (v/v:40/60) as eluent gave the ether of 3-(adamantan-2-ylidene-methoxymethyl)phenyl enol ester of [4,5-dimethoxy-2-(phenylacetylaminomethyl)phenyl]-acetic acid 2 (606 mg, 53%) in the form of a white powder. M.p. 95° C. 1H NMR (CDCl3, 300 MHz) δ 7.21 (t, J=7.9 Hz, 1H), 7.15-7.00 (m, 6H), 6.91 (t, J=2.3 Hz, 1H), 6.84 (ddd, J=7.9 Hz, 2.3 Hz, 0.8 Hz, 1H), 6.80 (s, 1H), 6.77 (s, 1H), 4.44 (d, J=5.3 Hz, 2H), 3.88 (s, 3H), 3.85 (s, 2H), 3.81 (s, 3H), 3.53 (s, 2H), 3.30 (s, 3H), 3.25 (br s, 1H), 2.66 (br s, 1H), 1.90-1.55 (m, 12H). 13C NMR (CDCl3, 75 MHz) δ 150.6, 148.6, 148.5, 142.6, 137.3, 134.9, 132.9, 129.4, 129.1, 128.9, 127.3, 127.1, 124.1, 122.1, 120.4, 113.5, 112.9, 58.0, 56.1, 56.0, 43.9, 41.4, 39.3, 39.1, 38.3, 37.2, 32.2, 30.3, 28.3. M.S. (Maldi-T of, positive mode) m/z 634.27 [M+K]+, 618.30 [M+Na]+. Analysis calculated for C37H41NO6: C=74.60, H=6.94 and N=2.35. Analysis measured: C=74.25, H=7.09 and N=2.41.

Workup

  1. concentrationThe mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-0d393a2f2c214ea0934f26478d779f93
Source dataset
uspto-grants-2011_06
Patent number
US07968735B2

Reaction notes

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