Tert-Butylamine → HCID 131727553, compound

HRID 2099883Notes

Reaction equation

HRID 2099883 reaction equation
C([O:4][C@@H:5]1[C@H:9]([O:10][CH2:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)[C@@:8]([CH2:28][O:29]C(=O)C)([CH2:22][O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[O:7][C@@:6]1([SiH:41]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[N:33]1[CH:40]=[CH:39][C:37](=[O:38])[NH:36][C:34]1=[O:35])(=O)C.C(N)(C)(C)C>CO>[C:24]([O:23][CH2:22][C@@:8]1([CH2:28][OH:29])[O:7][C@@:6]([SiH:41]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)([N:33]2[CH:40]=[CH:39][C:37](=[O:38])[NH:36][C:34]2=[O:35])[C@H:5]([OH:4])[C@@H:9]1[O:10][CH2:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1)([CH3:27])([CH3:26])[CH3:25]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 131727554HCID 131727554, compound

Product 1

HCID 131727553HCID 131727553, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of Compound 45 (34.9 g, 47.08 mmol) in anhydrous methanol (250 mL) was added tertbutylamine (26.3 mL, 250 mmol). After stirring at room temperature for 24 hours, the mixture was concentrated in vacuo, redissolved in EtOAc (0.8 L), washed with saturated aqueous NaHCO3, dried over anhydrous Na2SO4, filtered, evaporated and dried under high vacuum to yield Compound 46 (30.6 g, 99%) as a pale yellow foam.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. dissolutionredissolved in EtOAc (0.8 L)
  3. washwashed with saturated aqueous NaHCO3
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-412ae31e8c35438b8eceb00f738111ac
Source dataset
uspto-grants-2009_08
Patent number
US07569686B1

Reaction notes

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