Pivaloyl chloride → (3S*,5R*)-5-(2,2-Dimethyl-propionylamino)-piperidine-3-carboxylic acid ethyl-[4-(3-methoxy-propyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-amide

HRID 1698330Notes

Reaction equation

HRID 1698330 reaction equation
C1C2C(COC([N:18]3[CH2:23][C@@H:22]([C:24](=[O:44])[N:25]([CH2:42][CH3:43])[C:26]4[CH:27]=[CH:28][C:29]5[O:34][CH2:33][C:32](=[O:35])[N:31]([CH2:36][CH2:37][CH2:38][O:39][CH3:40])[C:30]=5[CH:41]=4)[CH2:21][C@@H:20]([NH2:45])[CH2:19]3)=O)C3C(=CC=CC=3)C=2C=CC=1.FC(F)(F)C([O-])=O.[C:53](Cl)(=[O:58])[C:54]([CH3:57])([CH3:56])[CH3:55]>CC#N>[CH2:42]([N:25]([C:26]1[CH:27]=[CH:28][C:29]2[O:34][CH2:33][C:32](=[O:35])[N:31]([CH2:36][CH2:37][CH2:38][O:39][CH3:40])[C:30]=2[CH:41]=1)[C:24]([C@H:22]1[CH2:21][C@@H:20]([NH:45][C:53](=[O:58])[C:54]([CH3:57])([CH3:56])[CH3:55])[CH2:19][NH:18][CH2:23]1)=[O:44])[CH3:43]

Participants

5

Reactant 3

HCID 62493Pivaloyl chlorideHCID 84468TrifluoroacetateHCID 69071792(3R*,5S*)-3-amino-5-{ethyl-[4-(3-methoxy-propyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-carbamoyl}-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester

Product 1

HCID 15984738(3S*,5R*)-5-(2,2-Dimethyl-propionylamino)-piperidine-3-carboxylic acid ethyl-[4-(3-methoxy-propyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-amide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound is prepared analogously as described in Example 61 using (3R*,5S*)-3-amino-5-{ethyl-[4-(3-methoxy-propyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-carbamoyl}-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester, trifluoroacetate and pivaloyl chloride. MS: 475.4 [M+H]+; tR (HPLC, Nucleosil C18; 5-100% CH3CN+0.1% TFA/H2O+0.1% TFA for 8 min, flow 1.5 ml/min): 4.29 min.

Workup

  1. custom4.29 min.

Sources & evidence

ORD record
ord-69b4dd78e86441e09c8d9888403ca4df
Source dataset
uspto-grants-2012_04
Patent number
US08163773B2

Reaction notes

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