Triethylamine → HCID 102526939, compound

HRID 1056861Notes

Reaction equation

HRID 1056861 reaction equation
[Si:1]([O:8][C@H:9]([C@@:11]1([NH:31][C:32]([N:34]([CH3:36])[CH3:35])=[O:33])[C:16](=[O:17])[C@@:15]2([CH2:18][OH:19])[C@H:13]([O:14]2)[C@@H:12]1[NH:20][C:21](=[O:30])[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CCN(CC)CC.[CH3:44][C:45]([Si:48](Cl)([C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([CH3:47])[CH3:46].[NH4+].[Cl-]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Si:1]([O:8][C@H:9]([C@@:11]1([NH:31][C:32]([N:34]([CH3:36])[CH3:35])=[O:33])[C:16](=[O:17])[C@@:15]2([CH2:18][O:19][Si:48]([C:45]([CH3:47])([CH3:46])[CH3:44])([C:55]3[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=3)[C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[C@H:13]([O:14]2)[C@@H:12]1[NH:20][C:21](=[O:30])[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH3:10])([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 94078tert-ButyldiphenylchlorosilaneHCID 102526945HCID 102526945, compound

Product 1

HCID 102526939HCID 102526939, compoundYield 76.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A flame-dried 25-mL round-bottomed flask was charged with alcohol 11 (1.0 g, 1.9 mmol, 1.0 equiv) and CH2Cl2 (9.5 mL). NEt3 (0.8 mL, 5.7 mmol, 3.0 equiv) and DMAP (0.023 g, 0.19 mmol, 0.1 equiv) were added and the solution was cooled 0° C. TBDPSCl (1.47 mL, 5.7 mmol, 3.0 equiv) was added dropwise and the reaction was warmed to rt and stirred for 8 h. Saturated NH4Cl(aq.) (10 mL) was added and the mixture was extracted with Et2O (3×15 mL). The combined organic extracts were washed with brine (10 mL), dried with magnesium sulfate, and concentrated in vacuo. The crude product was purified via flash chromatography (70:30 hexanes:EtOAc) to give the title compound as a pale yellow oil (1.1 g, 76%). Analytical data: [α]D19 −4.4 (c=0.70, CHCl3); 1H NMR (600 MHz, CDCl3): δ 7.67 (d, J=7.2 Hz, 2H), 7.62 (d, J=7.2 Hz, 2H), 7.44-7.30 (m, 11H), 5.68 (d, J=10.2 Hz, 1H), 5.23 (d, J=12.0 Hz, 1H), 4.97 (d, J=12.6 Hz, 1H), 4.74 (dd, J=3.0, 7.2 Hz, 1H), 4.70 (br s, 1H), 4.26 (d, J=12, 6 Hz, 1H), 4.11 (d, J=3.0 Hz, 1H), 4.03 (q, J=6.0 Hz, 1H), 3.92 (d, J=12.0 Hz, 1H), 2.68 (s, 6H), 1.19 (d, J=6.0 Hz, 3H), 1.01 (s, 9H), 0.92 (s, 9H), 0.13 (s, 6H); 13C NMR (150 MHz, CDCl3): δ 203.9, 156.8, 156.0, 136.7, 135.5, 135.4, 132.6, 132.3, 129.8, 129.7, 128.3, 128.1, 127.9, 127.8, 127.7, 74.1, 69.4, 66.4, 66.2, 60.8, 57.5, 52.2, 36.1, 26.6, 25.6, 19.1, 18.3, 17.8, −3.8, −4.8; LRMS (ESI+) Calcd. for C41H57N3O7Si2+H, 760.38. Found, 760.31. IR (thin film, cm−1) 3419, 2931, 2857, 2359, 1716, 1651, 1507, 1226, 1113, 828, 733; TLC (70:30 hexanes/EtOAc): Rf=0.30.

Workup

  1. temperaturethe reaction was warmed to rt
  2. extractionthe mixture was extracted with Et2O (3×15 mL)
  3. washThe combined organic extracts were washed with brine (10 mL)
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified via flash chromatography (70:30 hexanes:EtOAc)

Sources & evidence

ORD record
ord-f2226ddb467540909b907c690511e355
Source dataset
uspto-grants-2016_07
Patent number
US09399652B2

Reaction notes

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