Triethylamine → HCID 67061890, compound

HRID 910813Notes

Reaction equation

HRID 910813 reaction equation
[CH3:1][O:2][CH2:3][C@H:4]([CH3:51])[CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C@@H:14]2[C@@H:19]([O:20][CH2:21][C:22]3[CH:23]=[CH:24][C:25]4[O:30][CH2:29][CH2:28][N:27]([CH2:31][CH2:32][CH2:33][O:34][CH3:35])[C:26]=4[CH:36]=3)[CH2:18][N:17]([S:37]([C:40]3[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=3)(=[O:39])=[O:38])[C@@H:16]([CH2:47][C:48](O)=[O:49])[CH2:15]2)=[CH:10][CH:9]=1.ClC(N(C)C)=C(C)C.[C:60]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])(=[O:63])[NH:61][NH2:62].CCN(CC)CC>C(Cl)Cl>[C:65]([O:64][C:60]([NH:61][NH:62][C:48](=[O:49])[CH2:47][C@H:16]1[CH2:15][C@H:14]([C:11]2[CH:12]=[CH:13][C:8]([CH2:7][O:6][CH2:5][C@@H:4]([CH3:51])[CH2:3][O:2][CH3:1])=[CH:9][CH:10]=2)[C@@H:19]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]3[O:30][CH2:29][CH2:28][N:27]([CH2:31][CH2:32][CH2:33][O:34][CH3:35])[C:26]=3[CH:36]=2)[CH2:18][N:17]1[S:37]([C:40]1[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=1)(=[O:39])=[O:38])=[O:63])([CH3:68])([CH3:67])[CH3:66]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 70091tert-Butyl carbazateHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 67061895HCID 67061895, compound

Product 1

HCID 67061890HCID 67061890, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1 mmol of [(2R,4R,5R)-4-[4-((S)-3-methoxy-2-methyl-propoxymethyl)-phenyl]-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)-piperidin-2-yl]-acetic acid (example 1g) in 5 ml of CH2Cl2 is treated at RT with 1.5 mmol of 1-chloro-N,N,2-trimethylpropenylamine, and stirred at RT for 2.5 h. This solution is added slowly, at 0° C., to a solution of 5 mmol of tert-butyl carbazate [870-46-2] and 5 mmol of Et3N in 1 ml of CH2Cl2. The reaction mixture is stirred at 4° C. for 16.5 h, then quenched with H2O. The aqueous layer is extracted with CH2Cl2 (2×). The combined organic extracts are washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue is purified by flash chromatography (SiO2 60 F) to afford the title compound as a yellow oil. Rf=0.34 (EtOAc/Heptane 2:1); Rt=5.28 (gradient I).

Workup

  1. stirringThe reaction mixture is stirred at 4° C. for 16.5 h
  2. customquenched with H2O
  3. extractionThe aqueous layer is extracted with CH2Cl2 (2×)
  4. washThe combined organic extracts are washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by flash chromatography (SiO2 60 F)

Sources & evidence

ORD record
ord-fa8950b4ef2344b684f660fc98bb3744
Source dataset
uspto-grants-2011_09
Patent number
US08022068B2

Reaction notes

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