N,N-Diethylethanamine trihydrofluoride → HCID 66952297, compound

HRID 2190216Notes

Reaction equation

HRID 2190216 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[C:27]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:26]=1)[C:10]([O:12][C@H:13]([CH3:23])[CH2:14][O:15][Si](C(C)(C)C)(C)C)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].F.F.F.C(N(CC)CC)C>O1CCCC1>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[C:27]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:26]=1)[C:10]([O:12][C@H:13]([CH3:23])[CH2:14][OH:15])=[O:11])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 175505N,N-Diethylethanamine trihydrofluorideHCID 60207242HCID 60207242, compound

Product 1

HCID 66952297HCID 66952297, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(1R)-1-Methyl-2-(tert-butyldimethylsilyloxy)ethyl (2S)-2-[(tert-butoxy)carbonylamino]-3-[3,4-bis(phenylmethoxy)phenyl]propanoate (16) (4.7 g, 7.2 mmol) was dissolved in anhydrous tetrahydrofuran. Triethylamine trihydrofluoride (9.4 mL, 57.0 mmol) was slowly added. The mixture was stirred at room temperature for 4 hours. Removal of solvent under reduced pressure gave 3.8 g (98% yield) of the title compound. 1H NMR (400 MHz, CDCl3): δ 1.09 (d, J=6.4 Hz, 3H), 1.41 (s, 9H), 2.78 (s, 1H, br), 2.96 (m, 2H), 3.51 (m, 1H), 3.68 (m, 1H), 4.36 (dd, J=14.0, 6.4 Hz, 1H), 4.98 (m, 1H), 5.05 (d, 1H, NH), 5.10 (s, 4H), 6.66 (d, J=8.0 Hz, 1H), 6.77 (s, 1H), 6.83 (d, J=8.0 Hz, 1H), 7.26-7.43 (m, 10H).

Workup

  1. customRemoval of solvent under reduced pressure

Sources & evidence

ORD record
ord-5aebc785b86d4ba69cd11b34f6958508
Source dataset
uspto-grants-2012_12
Patent number
US08324273B2

Reaction notes

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