Triethylamine → HCID 23630517, compound

HRID 1929298Notes

Reaction equation

HRID 1929298 reaction equation
[CH2:1]([O:8][C:9]1[C:10]2[N:11]=[CH:12][N:13]([C:52]=2[N:53]=[C:54]([NH:56][C:57](=[O:66])[CH2:58][O:59][C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[N:55]=1)[C@@H:14]1[O:51][C@H:25]([CH2:26][O:27]C(C2C=CC=CC=2)(C2C=CC(OC)=CC=2)C2C=CC(OC)=CC=2)[C@@H:16]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH2:15]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC>C(Cl)Cl>[CH2:1]([O:8][C:9]1[C:10]2[N:11]=[CH:12][N:13]([C:52]=2[N:53]=[C:54]([NH:56][C:57](=[O:66])[CH2:58][O:59][C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[N:55]=1)[C@@H:14]1[O:51][C@H:25]([CH2:26][OH:27])[C@@H:16]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:19])[CH3:20])[CH2:15]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 23630721HCID 23630721, compound

Product 1

HCID 23630517HCID 23630517, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3% TCA (67.8 mL, 19.9 mmol) in CH2Cl2 is added to a solution of 8 (4.51 g, 4.97 mmol) dissolved in CH2Cl2 (100 mL) and stirred at room temperature for 4 minutes. Et3N (2.77 mL, 19.9 mmol) is added to the solution, and the solvent is removed under reduced pressure. The resulting solid is purified by column chromatography (silica, 90:10 CH2Cl2: EtOAc) to afford 9 as an off-white foam (2.56, 85.0%). 1H NMR (DMSO-d6) δ 10.69 (1H, s, N2H, exchanges with D2O), 8.47 (1H, s, H-8), 7.54 (2H, dd, J=8.4, J=1.6, PAc Ar), 7.42-7.34 (3H, m, Bn Ar), 7.31-7.26 (2H, m, Bn Ar), 6.97-6.92 (3H, m, PAc Ar), 6.33 (1H, t, J=6.8, H-1′), 5.63 (2H, s, CH2-Ph), 5.04 (2H, s, Pac-CH2), 4.94 (1H, t, J=5.4, 5′-OH, exchanges with D2O), 4.60 (1H, ddd, J=5.6, J=2.8, J=2.8, H-3′), 3.84 (1H, ddd, J=4.8, J=4.8, J=2.8, H-4′), 3.57 (1H, ddd, J=11.6, J=5.6, J=5.6, H-5′), 3.51 (1H, J=11.2, J=5.2, J=4.8, H-5′), 2.82 (1H, ddd, J=13.2, J=6.0, J=2.0, H-2′), 2.28 (1H, ddd, J=13.2, J=6.0, J=3.2, H-2′), 0.875 (9H, s, Si—C(CH3)3), 0.094 (3H, s, Si—CH3), 0.088 (3H, s, Si—CH3). Anal. (C31H39N5O6Si) C, H, N.

Workup

  1. customthe solvent is removed under reduced pressure
  2. customThe resulting solid is purified by column chromatography (silica, 90:10 CH2Cl2: EtOAc)

Sources & evidence

ORD record
ord-978f032f81514a7989eadfa411971c9c
Source dataset
uspto-grants-2012_05
Patent number
US08188055B2

Reaction notes

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