Triethylamine → HCID 42633023, compound

HRID 1674683Notes

Reaction equation

HRID 1674683 reaction equation
C(OC([N:11]1[CH2:16][C@H:15]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]3[O:27][CH2:26][CH2:25][N:24]([CH2:28][CH2:29][CH2:30][O:31][CH3:32])[C:23]=3[CH:33]=2)[C@@H:14]([C:34]2[CH:39]=[CH:38][C:37]([CH2:40][O:41][CH2:42][C@H:43]([O:45][CH2:46][CH3:47])[CH3:44])=[CH:36][CH:35]=2)[C@H:13]([CH2:48][NH2:49])[CH2:12]1)=O)C1C=CC=CC=1.CCN(CC)CC>C(Cl)Cl>[CH2:46]([O:45][C@H:43]([CH3:44])[CH2:42][O:41][CH2:40][C:37]1[CH:36]=[CH:35][C:34]([C@@H:14]2[C@@H:15]([O:17][CH2:18][C:19]3[CH:20]=[CH:21][C:22]4[O:27][CH2:26][CH2:25][N:24]([CH2:28][CH2:29][CH2:30][O:31][CH3:32])[C:23]=4[CH:33]=3)[CH2:16][NH:11][CH2:12][C@H:13]2[CH2:48][NH2:49])=[CH:39][CH:38]=1)[CH3:47]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 67336086HCID 67336086, compound

Product 1

HCID 42633023HCID 42633023, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.4 mmol of 4-nitrophenylformiate are added to a solution of 1 mmol of (3R,4R,5R)-3-aminomethyl-4-[4-((R)-2-ethoxy-propoxymethyl)-phenyl]-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-piperidine-1-carboxylic acid benzyl ester (example 6a) in 10 ml of CH2Cl2 under argon followed by the addition of 1 mmol of Et3N. After 60 min, the reaction mixture is evaporated. The residue is purified by flash chromatography (SiO2 60F) to afford the title compound, which is identified based on the Rf value.

Workup

  1. customthe reaction mixture is evaporated
  2. customThe residue is purified by flash chromatography (SiO2 60F)

Sources & evidence

ORD record
ord-77cce147e8b1466280242ced8c4a9431
Source dataset
uspto-grants-2011_08
Patent number
US08003640B2

Reaction notes

Loading…