Benzenepropanoic acid → HCID 88142219, compound

HRID 1587597Notes

Reaction equation

HRID 1587597 reaction equation
C1(C(N[C@H:9]([C:17]([NH:19][C@H:20]([C:25]([NH:27][C@@H:28]([CH2:37][CH:38]2[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]2)[CH:29]([P:31]([O:35][CH3:36])([O:33][CH3:34])=[O:32])[OH:30])=[O:26])[CH2:21][CH:22]([CH3:24])[CH3:23])=[O:18])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=O)CCCC1.C(O)(=O)CCC1C=CC=CC=1.O.OC1C2N=NNC=2C=CC=1.C(N(CC)C(C)C)(C)C.Cl.CN(C)CCCN=C=NCC>C(#N)C>[O:18]=[C:17]([NH:19][C@H:20]([C:25]([NH:27][C@@H:28]([CH2:37][CH:38]1[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]1)[C@@H:29]([P:31]([O:35][CH3:36])([O:33][CH3:34])=[O:32])[OH:30])=[O:26])[CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 5

HCID 107Benzenepropanoic acidHCID 81531Diisopropylethylamine2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10009053HCID 10009053, compoundHCID 178526939HCID 178526939, compound

Product 1

HCID 88142219HCID 88142219, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

The title A compound of Example 5 (622.2 mg, 1.5 mmol) was added to a solution of hydrocinnamic acid (225.3 mg, 1.5 mmol) in acetonitrile (7.5 mL) and cooled to 0° C. Hydroxybenzotriazole hydrate (229.5 mg, 1.5 mmol), N,N-diisopropylethylamine (287 μl, 1.65 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added sequentially. After 64 hours at 0° C., additional N,N-diisopropylethylamine (52 μl, 0.3 mmol) was added and the reaction was allowed to proceed for 24 hours at 25° C. The reaction mixture was then concentrated and stirred with pH 4.01 buffer solution for 10 minutes. The resulting precipitate was filtered, washed sequentially with pH 4.01 buffer (3×50 mL) and water (3×50 mL), and dried in vacuo yielding 476.9 mg of crude product. Purification by flash chromatography afforded 253.6 mg of product, which was crystallized from hexane/ethyl acetate yielding 230.6 mg of the title compound, m.p. 157° C., [α]D =-74.6° (c=0.50, CH3OH).

Workup

  1. waitto proceed for 24 hours at 25° C
  2. concentrationThe reaction mixture was then concentrated
  3. filtrationThe resulting precipitate was filtered
  4. washwashed sequentially with pH 4.01 buffer (3×50 mL) and water (3×50 mL)
  5. customdried in vacuo
  6. customyielding 476.9 mg of crude product
  7. customPurification by flash chromatography

Sources & evidence

ORD record
ord-a3cfa548dcec4cb888b3fea9dc925e9e
Source dataset
uspto-grants-1993_06
Patent number
US05217958

Reaction notes

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