Tetrabutylammonium Fluoride → N-[2-chloro-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]-6-methylbenzoyl]-3-[[(1,1-dimethylethoxy)carbonyl]amino]-L-alanine, methyl ester

HRID 2270828Notes

Reaction equation

HRID 2270828 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl:19][C:20]1[CH:42]=[C:41]([C:43]([NH:45][CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[C:49]([O:53][Si](C(C)(C)C)(C)C)[CH:48]=2)=[O:44])[CH:40]=[C:39]([CH3:61])[C:21]=1[C:22]([NH:24][C@H:25]([C:35]([O:37][CH3:38])=[O:36])[CH2:26][NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[O:23]>O1CCCC1.C(OCC)(=O)C>[Cl:19][C:20]1[CH:42]=[C:41]([C:43]([NH:45][CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[C:49]([OH:53])[CH:48]=2)=[O:44])[CH:40]=[C:39]([CH3:61])[C:21]=1[C:22]([NH:24][C@H:25]([C:35]([O:37][CH3:38])=[O:36])[CH2:26][NH:27][C:28]([O:30][C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29])=[O:23]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131723026N-[2-chloro-4-[[[[3-[[(1,1-dimethylethyl) dimethylsilyl]oxy]phenyl]methyl]amino]carbonyl]-6-methylbenzoyl]-3-[[(1,1-dimethylethoxy)carbonyl]amino]-L-alanine, methyl ester

Product 1

HCID 131723027N-[2-chloro-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]-6-methylbenzoyl]-3-[[(1,1-dimethylethoxy)carbonyl]amino]-L-alanine, methyl esterYield 97.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of tetra-n-butylammonium fluoride in tetrahydrofuran (1 M; 1.78 mL, 1.78 mmol) was added in two portions to a solution of N-[2-chloro-4-[[[[3-[[(1,1-dimethylethyl) dimethylsilyl]oxy]phenyl]methyl]amino]carbonyl]-6-methylbenzoyl]-3-[[(1,1-dimethylethoxy)carbonyl]amino]-L-alanine, methyl ester (1.03 g, 1.62 mmol) in dry tetrahydrofuran (20 mL). The solution was stirred at room temperature for 30 min, then diluted with ethyl acetate (100 mL) and washed with water (25 mL) and brine (25 mL). The solution was dried (MgSO4), filtered, evaporated, held under high vacuum for 2.5 h, and then chromatographed (60-70% ethyl acetate/petroleum ether) to give N-[2-chloro-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]-6-methylbenzoyl]-3-[[(1,1-dimethylethoxy)carbonyl]amino]-L-alanine, methyl ester (0.82 g, 97%) as a white foam.

Workup

  1. washwashed with water (25 mL) and brine (25 mL)
  2. dry with materialThe solution was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. waitheld under high vacuum for 2.5 h
  6. customchromatographed (60-70% ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-22619c18550a4a1bb980f3d449a06d7c
Source dataset
uspto-grants-2001_12
Patent number
US06331640B1

Reaction notes

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