HCID 57870323, compound → (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 1698331Notes

Reaction equation

HRID 1698331 reaction equation
C1C2C(COC([N:18]3[CH2:23][C@H:22]([NH:24][C:25]([O:27]C(C)(C)C)=O)[CH2:21][C@H:20]([C:32]([OH:34])=O)[CH2:19]3)=O)C3C(=CC=CC=3)C=2C=CC=1.[CH2:35]([NH:37][C:38]1[CH:39]=[CH:40][C:41]2[O:46][CH2:45][C:44](=[O:47])[N:43]([CH2:48][CH2:49][CH2:50][O:51][CH3:52])[C:42]=2[CH:53]=1)[CH3:36]>>[CH2:35]([N:37]([C:38]1[CH:39]=[CH:40][C:41]2[O:46][CH2:45][C:44](=[O:47])[N:43]([CH2:48][CH2:49][CH2:50][O:51][CH3:52])[C:42]=2[CH:53]=1)[C:32]([C@H:20]1[CH2:21][C@@H:22]([NH:24][C:25](=[O:27])[C:20]([CH3:32])([CH3:21])[CH3:19])[CH2:23][NH:18][CH2:19]1)=[O:34])[CH3:36]

Participants

3

Reactant 2

HCID 57870323HCID 57870323, compoundHCID 598177316-(Ethylamino)-4-(3-methoxypropyl)-2H-1,4-benzoxazin-3(4H)-one

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

Procedure

The title compound is prepared analogously as described in Example 92A. using (3S*,5R*)-5-tert-butoxycarbonylamino-piperidine-1,3-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester and 6-ethylamino-4-(3-methoxy-propyl)-4H-benzo[1,4]oxazin-3-one. The product is purified by preparative HPLC (YMC Pack Pro C18, 10-100% CH3CN+0.1% TFA/H2O+0.1% TFA, 20 min, flow 20 ml/min); tR (HPLC, Nucleosil C18; 5-100% CH3CN+0.1% TFA/H2O+0.1% TFA for 8 min, flow 1.5 ml/min): 5.47 min.

Workup

  1. customThe product is purified by preparative HPLC (YMC Pack Pro C18, 10-100% CH3CN+0.1% TFA/H2O+0.1% TFA, 20 min, flow 20 ml/min)
  2. customtR (HPLC, Nucleosil C18; 5-100% CH3CN+0.1% TFA/H2O+0.1% TFA for 8 min, flow 1.5 ml/min)
  3. custom5.47 min.

Sources & evidence

ORD record
ord-bb7e284edacb4d89959976379d85bd2c
Source dataset
uspto-grants-2012_04
Patent number
US08163773B2

Reaction notes

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