Triethylamine → HCID 66860793, compound

HRID 2179787Notes

Reaction equation

HRID 2179787 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:12][C@H:11]([C:13]([OH:15])=O)[C:10]1([CH3:17])[CH3:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.Cl.[NH2:29][CH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33].CCN(CC)CC>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:12][C@H:11]([C:13]([NH:29][CH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33])=[O:15])[C:10]1([CH3:17])[CH3:16])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 15819069HCID 15819069, compound

Product 1

HCID 66860793HCID 66860793, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred solution of (1S,3R)-3-(tert-butoxycarbonylamino)-2,2-dimethylcyclobutanecarboxylic acid (0.3 g, 1.234 mmol) in DCM (5 ml) EDCI (0.284 g, 1.48 mmol) and HOBt (0.2 g, 1.48 mmol) were added at about 0° C., after 10 minutes methyl 3-aminopropanoate hydrochloride (0.254 g, 2.47 mmol) and Et3N (0.9 ml, 6.17 mmol) in DCM (5 ml) were added drop wise and the reaction mass was allowed to stir at room temperature for about 16 hours. After completion of the reaction (monitored by TLC), the reaction mixture was diluted with DCM and washed with water and saturated NaHCO3 solution, then washed with aqueous 1N HCl, then washed with water and saturated brine, and the organic layer was concentrated under reduced pressure, the resulting crude was purified by silica gel column (100-200 mesh, elution 70% EtOAC in hexane) to afford the title compound as solid. Wt: 0.336 g; Yield: 88.9%; 1H NMR (300 MHz, CDCl3): δ 5.89 (brs, 1H), 4.79 (d, 1H, J=8.1 Hz), 3.88-3.73 (m, 1H), 3.70 (s, 3H), 3.59-3.42 (m, 2H), 2.54-2.51 (m, 2H), 2.39-2.20 (m, 2H), 2.11-1.99 (m, 1H), 1.43 (s, 9H), 1.26 (s, 3H), 0.87 (s, 3H); Mass: [M+Na]+ 351 (100%); IR (KBr, cm−1): 3359, 3319, 2973, 1737, 1696, 1667, 1539, 1454, 1366, 1271, 1254, 1176, 1051, 1024, 782, 683; M.R: 98.6° C.-100.2° C.

Workup

  1. additionwere added drop wise
  2. customAfter completion of the reaction (monitored by TLC)
  3. washwashed with water and saturated NaHCO3 solution
  4. washwashed with aqueous 1N HCl
  5. washwashed with water and saturated brine
  6. concentrationthe organic layer was concentrated under reduced pressure
  7. customthe resulting crude was purified by silica gel column (100-200 mesh, elution 70% EtOAC in hexane)

Sources & evidence

ORD record
ord-86839558dd884d839186b19e8cd8c535
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

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