Hydrochloric Acid → HCID 86640481, compound

HRID 389799Notes

Reaction equation

HRID 389799 reaction equation
Cl.[NH:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].[O:17]1[CH2:21][CH2:20][CH2:19][C@@H:18]1[C:22](O)=[O:23].CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.C(N=C=NCCCN(C)C)C.Cl>ClCCl>[O:17]1[CH2:21][CH2:20][CH2:19][C@@H:18]1[C:22]([N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])=[O:23]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733413Proline benzyl ester hydrochlorideHCID 2734707Tetrahydro-2-furoic acid, (+)-

Product 1

HCID 86640481HCID 86640481, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred suspension of (S)-benzyl pyrrolidine-2-carboxylate hydrochloride (5.63 g, 23.3 mmol), (R)-tetrahydrofuran-2-carboxylic acid (2.24 mL, 23.3 mmol), DIPEA (10.2 mL, 58.3 mmol), and HOBt (3.15 g, 23.3 mmol) in dry dichloromethane (100 mL) at 25° C. was added 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (4.45 g, 23.3 mmol) in one portion. The mixture was stirred at 25° C. for 16 h then 1N HCl (50 mL) was added. The organic phase was separated, washed with saturated sodium bicarbonate solution, dried with Na2SO4, filtered and concentrated to afford intermediate (S)-benzyl 1-((R)-tetrahydrofuran-2-carbonyl)pyrrolidine-2-carboxylate as a yellow oil which was carried forward directly.

Workup

  1. customThe organic phase was separated
  2. washwashed with saturated sodium bicarbonate solution
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a8fa783657b8457e88a2dc4c45aa9b60
Source dataset
uspto-grants-2013_02
Patent number
US08383094B2

Reaction notes

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