Tetrabutylammonium Fluoride → HCID 20698898, compound

HRID 383119Notes

Reaction equation

HRID 383119 reaction equation
[CH3:1][O:2][C:3](=[O:47])[C@H:4]([CH2:43][CH2:44][S:45][CH3:46])[NH:5][C:6](=[O:42])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:35])[C@@H:15]2[CH2:19][CH:18]([O:20][Si](C(C)(C)C)(C)C)[CH2:17][N:16]2[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:9][C:8]=1[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:47])[C@H:4]([CH2:43][CH2:44][S:45][CH3:46])[NH:5][C:6](=[O:42])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:35])[C@@H:15]2[CH2:19][CH:18]([OH:20])[CH2:17][N:16]2[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:9][C:8]=1[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 20698900HCID 20698900, compound

Product 1

HCID 20698898HCID 20698898, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1.82 g (2.65 mmol) of {4-[N-Boc-4-(t-butyldimethylsilyloxy)-prolinyl]amino-2-phenylbenzoyl}methionine methyl ester, prepared as in Example 169B, in 20 ml of THF was added 3 ml (3 mmol) of 1 M tetra-n-butylammonium fluoride in THF. The reaction mixture was stirred overnight, diluted with ethyl acetate, and washed 3 times with water. The combined aqueous washings were extracted 3 times with ethyl acetate. The combined organic fractions were dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (ethyl acetate) to obtain 864 mg (57%) of [4-(N-Boc-4-hydroxyprolinyl)amino-2-phenylbenzoyl]methionine methyl ester as a white solid: mp 121-123° C. ; [α]25D−53.3 (c=0.43, CHCl3);

Workup

  1. washwashed 3 times with water
  2. extractionThe combined aqueous washings were extracted 3 times with ethyl acetate
  3. dry with materialThe combined organic fractions were dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-0c4e92e2a6b540be974f50c88ce71f3f
Source dataset
uspto-grants-2001_10
Patent number
US06310095B1

Reaction notes

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