Triethylamine → HCID 67272744, compound

HRID 601709Notes

Reaction equation

HRID 601709 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:40]=[C:41]([F:43])[CH:42]=1)[CH2:5][C@@H:6]([C@@H:10]([CH:12]1[CH2:21][C:20]2[C:15](=[C:16]([O:22][Si:23]([CH:30]([CH3:32])[CH3:31])([CH:27]([CH3:29])[CH3:28])[CH:24]([CH3:26])[CH3:25])[CH:17]=[CH:18][CH:19]=2)[CH2:14][N:13]1[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[OH:11])C(O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:51])C=CC=CC=1.C([N:63]([CH2:66]C)CC)C>C1(C)C=CC=CC=1>[F:43][C:41]1[CH:40]=[C:4]([CH:3]=[C:2]([F:1])[CH:42]=1)[CH2:5][C@H:6]1[C@@H:10]([C@H:12]2[CH2:21][C:20]3[C:15](=[C:16]([O:22][Si:23]([CH:30]([CH3:32])[CH3:31])([CH:24]([CH3:25])[CH3:26])[CH:27]([CH3:29])[CH3:28])[CH:17]=[CH:18][CH:19]=3)[CH2:14][N:13]2[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[O:11][C:66](=[O:51])[NH:63]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 67271210HCID 67271210, compound

Product 1

HCID 67272744HCID 67272744, compoundYield 29.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (2S,3S)-2-(3,5-difluorobenzyl)-3-(2-(tert-butoxycarbonyl)-8-(triisopropylsilyloxy)-1,2,3,4-tetrahydroisoquinolin-3-yl)-3-hydroxypropanoic acid (Step F (10), 2.0 g, 2.57 mmol) in toluene (150 mL) was added diphenylphosphoryl azide (1.13 g, 4.12 mmol) and triethyl amine (649 mg, 6.43 mmol.). This reaction mixture was brought to 50° C. for 2 h and 100° C. for 3 h. The mixture was concentrated under vacuum and purified by silica gel Flash Chromatography to give 470 mg of the title compound: 1H NMR (CDCl3, 500 MHz) δ 1.12 (18H, m), 1.28-1.36 (3H, m), 1.48 (9H, s), 2.71 (1H, m), 3.08 (2H, s), 3.18-3.22 (1H, m), 3.82 (1H, m), 4.59 (1H, m), 4.76-5.04 (2H, m), 5.11 (1H, s), 6.67-6.77 (5H, m), 7.06 (1H, m).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. custompurified by silica gel Flash Chromatography

Sources & evidence

ORD record
ord-f3e740f6df9541c8b911537ac69eaae1
Source dataset
uspto-grants-2011_03
Patent number
US07902218B2

Reaction notes

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