Thioglycolic Acid → HCID 86666542, compound

HRID 1397129Notes

Reaction equation

HRID 1397129 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])(C)C.[C:13]([OH:17])(=O)[CH2:14][SH:15].[C:18]1(C)C=CC=CC=1>>[SH:15][CH2:14][C:13]([NH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][CH2:8][CH:11]=[CH2:18])=[O:17]

Participants

4

Reactant 3

HCID 1133Thioglycolic AcidHCID 1140TolueneHCID 2735700tert-Butyl (3-aminopropyl)carbamate

Product 1

HCID 86666542HCID 86666542, compoundYield 42%

Conditions

Temperature
115 °C

Procedure

To a solution of tert-butyl 3-aminopropylcarbamate (85b, 2 g, 11.48 mmoles) in toluene (8 mL), in a pressure tube, was added 900 μL of thioglycolic acid (12.95 mmoles). Argon was bubbled through the solution for 15 min, and the mixture was capped and heated to 115° C. (bath temperature) for 24 h. The solution was then concentrated to dryness in vacuo and the residue was subjected to SiO2 chromatography on a Biotage™ flash chromatography system using 25-0% hexanes in EtOAc as the eluent to furnish 91 (1.19 g, 4.77 mmoles, 42% yield) as a colourless oil. 1H NMR (400 MHz, CDCl3) δ 1.65 (quintet, J=6.3 Hz, 2H), 1.94 (t, J=9.0 Hz, 1H), 3.17 (t, J=6.2, 2H), 3.24 (d, J=8.9 Hz, 2H), 3.33 (q, J=6.3 Hz, 2H), 4.11 (q, J=7.1 Hz, 1H), 4.87 (broad s, 1H), 7.12 (broad s, 1H).

Workup

  1. customArgon was bubbled through the solution for 15 min
  2. customthe mixture was capped
  3. concentrationThe solution was then concentrated to dryness in vacuo

Sources & evidence

ORD record
ord-46dfd0f919a04fee9f54cccebb3357f4
Source dataset
uspto-grants-2014_12
Patent number
US08901072B2

Reaction notes

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