Ammonia → HCID 70298293, compound

HRID 2288280Notes

Reaction equation

HRID 2288280 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:43][CH3:44])=[C:5]([C:9]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[O:10][CH2:11][C@H:12]2[O:16][C@@H:15]([N:17]3[CH:25]=[C:23]([CH3:24])[C:21](=[O:22])[NH:20][C:18]3=[O:19])[CH2:14][C@@H:13]2[CH2:26]OC(=O)C)[CH:6]=[CH:7][CH:8]=1.N>CO>[CH3:1][O:2][C:3]1[C:4]([O:43][CH3:44])=[C:5]([C:9]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[O:10][CH2:11][C@H:12]2[O:16][C@@H:15]([N:17]3[CH:25]=[C:23]([CH3:24])[C:21](=[O:22])[NH:20][C:18]3=[O:19])[CH2:14][C@@H:13]2[CH3:26])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 70297501HCID 70297501, compound

Product 1

HCID 70298293HCID 70298293, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

Compound 185 (0.70 g, 1.17 mmol) was dissolved in dry methanol. The reaction was cooled to 0° C. and NH3 in MeOH (1.5 ml, Ca. 9 M) was added dropwise via syringe. The reaction mixture was allowed to warm gradually to room temperature. After stirring for 24 hours the solution was concentrated to dryness, and the residue was chromatographed on a silica gel column with EtOAc/Hexane (6:4-8:2) as eluent to give 186 (0.40 g, 61%). 1H NMR (CDCl3): δ8.68 (br, 1 H, NH), 7.61 (m, 1 H, Tr), 7.43 (d, 1 H, J=1.1 Hz, H-6), 7.33-7.28 (m, 9 H, Tr), 6.85-6.82 (m, 4 H, Tr), 6.14 (dd, 1 H, J=4.7, 6.7 Hz, H-1'), 3.99-3.97 (m, 1 H, H-4'), 3.79 (s, 6 H, OCH3), 3.64-3.61 (m, 2 H, CH2OH), 3.51 (dd, 2 H, J=3,6, 10.5 Hz, H-5') 3.36 (dd, 1H, J=3.6, 10.5 Hz, H-5"), 2.62-2.60 (m, 1 H, H-3'), 2.35-2.31 (m, 1 H, H-2'), 2.24-2.20 (m, 1 H, H-2"), 2.12 (m, 1 H, OH), 2.05 (s, 3 H, COCH3), 1.52 (s, 3 H, CH3); 13C NMR (CDCl3): 163.7 (C4), 158.6, 150.3 (C2), 144.3, 135.7 (C6), 135.4, 130.1, 128.0 & 127.9 (d), 127.1, 113.2, 110.7 (C5), 86.9, 85.1 (C1'), 82.3 (C4'), 64.1 (C5'), 63.1, 55.2, 41.5 (C3'), 32.8 (C2'), 12.0.

Workup

  1. temperatureto warm gradually to room temperature
  2. concentrationwas concentrated to dryness
  3. customthe residue was chromatographed on a silica gel column with EtOAc/Hexane (6:4-8:2) as eluent

Sources & evidence

ORD record
ord-11691795a7e045eb9459d8bcb1f2ad45
Source dataset
uspto-grants-2000_07
Patent number
US06087482

Reaction notes

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