Dicyclohexylcarbodiimide → HCID 56623680, compound

HRID 652749Notes

Reaction equation

HRID 652749 reaction equation
C1([NH2+]C2CCCCC2)CCCCC1.[C:14]([NH:21][C@H:22]([C:44]([O-])=[O:45])[CH2:23][S:24][C:25]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].Cl.[CH3:48][O:49][C:50](=[O:53])[CH2:51][NH2:52].ON1C(=O)CCC1=O.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[CH3:48][O:49][C:50](=[O:53])[CH2:51][NH:52][C:44](=[O:45])[C@H:22]([CH2:23][S:24][C:25]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[NH:21][C:14]([O:16][C:17]([CH3:20])([CH3:18])[CH3:19])=[O:15]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 122755Glycine methyl ester hydrochlorideHCID 131715183HCID 131715183, compound

Product 1

HCID 56623680HCID 56623680, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of compound (XX) (19.33 g, 30.0 mmol), glycine methyl ester hydrochloride (see Curtis and Goebel, J. Prakt. Chem., 37:150, (1888)) (3.47 g, 30.0 mmol) and N-hydroxysuccinimide (3.46 g, 30.1 mmol) was cooled to 0° C., then treated with a solution of DCC (6.87 g, 33.4 mmol) in CH2Cl2 (20 ml). The mixture was stirred, cold, for 30 minutes, then at room temperature for 3 hours. The precipitate was filtered off, washed with CH2Cl2, and the combined filtrate and washings were washed with 1M aqueous KHS04, 5% aqueous NaHCO3 and saturated brine, dried (MgSO4) and evaporated. Recrystallization of the resulting solid gave compound (XXI) (12.3 g, 77%), mp 167°-9°.

Workup

  1. waitat room temperature for 3 hours
  2. filtrationThe precipitate was filtered off
  3. washwashed with CH2Cl2
  4. washthe combined filtrate and washings were washed with 1M aqueous KHS04, 5% aqueous NaHCO3 and saturated brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customRecrystallization of the resulting solid

Sources & evidence

ORD record
ord-57952502cdce4c57b5e3d02c57398da7
Source dataset
uspto-grants-1987_06
Patent number
US04673562

Reaction notes

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