Ethoxyacetic acid → HCID 9932172, compound

HRID 258283Notes

Reaction equation

HRID 258283 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C@:9]23[CH2:24][C@H:16]([C:17]4[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][C:22]=42)[C:15]2[C:10]3=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:4][CH2:3]1.CN(C1C=CC=CN=1)C.Cl.C(N=C=NCCCN(C)C)C.[CH2:46]([O:48][CH2:49][C:50](O)=[O:51])[CH3:47].[OH-].[Na+]>C(Cl)Cl>[Cl:23][C:20]1[CH:19]=[CH:18][C:17]2[C@H:16]3[CH2:24][C@:9]([CH2:8][N:5]4[CH2:6][CH2:7][CH:2]([NH:1][C:50](=[O:51])[CH2:49][O:48][CH2:46][CH3:47])[CH2:3][CH2:4]4)([C:10]4[C:15]3=[CH:14][CH:13]=[CH:12][CH:11]=4)[C:22]=2[CH:21]=1

Participants

7

Reactant 5

HCID 12301Ethoxyacetic acidHCID 14798Sodium HydroxideHCID 218852-DimethylaminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57251661HCID 57251661, compound

Product 1

HCID 9932172HCID 9932172, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-amino-1-[(9S,10S)-2-chloro-9,10-dihydro-9,10-methanoanthracene-9-ylmethyl]piperidine (752 mg, 2.22 mmol), dimethylaminopyridine (542 mg, 4.44 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (848 mg, 4.44 mmol), in methylene chloride (15 mL) was added ethoxyacetic acid (0.25 mL, 2.44 mmol). After stirring for 18 h, the mixture was treated with 1N sodium hydroxide (75 mL), and extracted with methylene chloride (3×75 mL). The combined extracts were washed with 1N sodium hydroxide (2×75 mL) and brine (50 mL), dried (sodium sulfate), filtered and concentrated to give a milky white syrup. Chromatography of this material over silica gel (eluant: ethyl acetate) provided the title compound as a colorless glass (807 mg, 86%), mp 68.0°-70.0° C.; MS(CI): 425 (M+H); [α]D23 =+41° (c=0.01, CHCl3); NMR (300 MHz,DMSO-d6): 1.13(t, 3H, J=7.0 Hz), 1.49(m, 2H), 1.61(m, 2H), 2.26(m, 2H, J=11.9 Hz), 2.46(br s, 2H), 2.94(m, 2H), 3.33(m, part. submerged, 2H), 3.43(q, 2H, J=7.0 Hz), 3.62(m, 1H), 3.78(s, 2H), 4.33(s, 1H), 6.94(m, 3H), 7.23(br m, 4H), 7.48(d, 1H, J=8.3 Hz).

Workup

  1. extractionextracted with methylene chloride (3×75 mL)
  2. washThe combined extracts were washed with 1N sodium hydroxide (2×75 mL) and brine (50 mL)
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a milky white syrup

Sources & evidence

ORD record
ord-b349129866c34e568d3bcba6039475e6
Source dataset
uspto-grants-1993_11
Patent number
US05266570

Reaction notes

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