Morpholine → 2-(Tert-butoxycarbonylamino)indan-5-carboxylic acid morpholinamide

HRID 48434Notes

Reaction equation

HRID 48434 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:18]([OH:20])=[O:19])[CH:15]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.C(N(CC)CC)C.CN(C1C=CC=CN=1)C>C(Cl)Cl>[N:21]1([C:6]([NH2:8])=[O:5])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:18]([OH:20])=[O:19])[CH:15]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 227195982-((tert-butoxycarbonyl)amino)-2,3-dihydro-1H-indene-5-carboxylic acid

Product 1

HCID 1317243662-(Tert-butoxycarbonylamino)indan-5-carboxylic acid morpholinamideYield 161.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using 2-(tert-butoxycarbonylamino)-5-carboxyindan (1.01 g, 3.6 mmol), morpholine (0.48 ml, 5.5 mmol), triethylamine (3.6 ml, 26 mmol), propanephosphonic acid anhydride (5.3 ml), dimethylaninopyridine (a catalytic amount) and methylene chloride (27 ml), a similar procedure to a) in Production Example 218 was carried out. The product obtained was purified by silica gel chromatography (methylene chloride:methanol=95:5) to obtain 2-(tert-butoxycarbonylamino)indan-5-carboxylic acid morpholinamide (1.0 g, 2.9 mmol) having the following physical properties:

Workup

  1. customThe product obtained
  2. customwas purified by silica gel chromatography (methylene chloride:methanol=95:5)

Sources & evidence

ORD record
ord-9668d1e7b84742cfb10b4d58ae111297
Source dataset
uspto-grants-2004_03
Patent number
US06703421B1

Reaction notes

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