1,2-Dichloroethane → HCID 14036261, compound

HRID 2361575Notes

Reaction equation

HRID 2361575 reaction equation
C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH3:24][O:25][C:26]([CH:28]1[CH2:32][C:31]2([S:37][CH2:36][CH2:35][CH2:34][S:33]2)[CH2:30][N:29]1C(=O)C(N)C(C)(C)C)=[O:27]>C(Cl)Cl>[CH3:24][O:25][C:26]([CH:28]1[CH2:32][C:31]2([S:33][CH2:34][CH2:35][CH2:36][S:37]2)[CH2:30][NH:29]1)=[O:27]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 21054030HCID 21054030, compound

Product 1

HCID 14036261HCID 14036261, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

L-Boc-cyclohexyl glycine (154 mg, Bachem), EDC (115 mg), HOBt (81 mg), and DIEA (284 mg) in CH2Cl2 (1 mL) was treated with amine salt 29 (189 mg) in CH2Cl2 (2 mL) and the mixture stirred for 2 hours. The mixture was partitioned between ethyl acetate and 1.0 N HCl, the organics washed with sodium bicarbonate, 1.0 N glycine sodium salt solution, 10% potassium carbonate solution and brine then dried over sodium sulfate, filtered, and concentrated in vacuo. Purification on a plug of silica gel eluting with 30% EtOAc/hexanes afforded 221 mg (70%) of 2-[2-tert-butoxycarbonylamino-2-cyclohexyl-acetylamino)-3,3-dimethyl-butyryl]-6,10-dithia-2-aza-spiro[4.5]decane-3-carboxylic acid methyl ester 30 as a white solid.

Workup

  1. customThe mixture was partitioned between ethyl acetate and 1.0 N HCl
  2. washthe organics washed with sodium bicarbonate, 1.0 N glycine sodium salt solution, 10% potassium carbonate solution and brine
  3. dry with materialthen dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification on a plug of silica gel eluting with 30% EtOAc/hexanes

Sources & evidence

ORD record
ord-4d47a927902d4e199b2fd55019743690
Source dataset
uspto-grants-2014_04
Patent number
US08691758B2

Reaction notes

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