Dichloromethane → HCID 70469043, compound

HRID 1982623Notes

Reaction equation

HRID 1982623 reaction equation
[NH2:1][CH:2]([CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:3][S:4][CH2:5][C:6]([OH:8])=[O:7].[C:13]([N:23]1[CH2:30][CH2:29][CH2:28][C@H:24]1[C:25]([OH:27])=O)([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14].ON1C2C=C[CH:39]=[CH:40][C:35]=2N=N1.Cl[CH2:42]Cl>>[C:17]1([CH2:16][O:15][C:13]([N:23]2[CH2:30][CH2:29][CH2:28][CH:24]2[C:25]([NH:1][CH:2]([CH2:3][S:4][CH2:5][C:6]([O:8][C:40]([CH3:39])([CH3:35])[CH3:42])=[O:7])[CH2:9][CH:10]([CH3:12])[CH3:11])=[O:27])=[O:14])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 757711-HydroxybenzotriazoleHCID 101987Benzyloxycarbonyl-L-prolineHCID 23316662HCID 23316662, compound

Product 1

HCID 70469043HCID 70469043, compound

Conditions

Temperature
0 °C

Procedure

7.51 g (0.03 mol) of (S)-1,1-dimethylethyl ester, [(2-amino-4-methylpentyl)thio]-acetic acid, 7.61 g (0.03 mol) carbobenzyloxy-L-proline, and 4.08 g (0.03 mol) 1-hydroxybenzotriazole are dissolved in 100 ml dichloromethane. The solution is cooled to 0° C. and 6.34 g (0.03 mol) of N,N-dicyclohexylcarbodiimide is added all at once. The reaction is kept at 0° C. for three days. The reaction mixture is filtered and the filtrate concentrated on a rotary evaporator. The residue is dissolved in ether, washed with 10% aqueous citric acid solution. The ether solution is dried over magnesium sulfate, filtered, and concentrated to a white solid. The solid is chromatographed on 230-400 mesh silica gel, eluting with dichloromethane followed by 3% methanol in dichloromethane. One obtains 10.99 g of [S-(R*,R*)]-phenylmethyl-2-[[[1-[[[2-(1,1-dimethylethoxy)-2-oxoethyl]thio]methyl]-3-methylbutyl]amino]carbonyl]-1-pyrrolidinecarboxylate; [α]D25 -11.6° (c 1.21, methanol).

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate concentrated on a rotary evaporator
  3. dissolutionThe residue is dissolved in ether
  4. washwashed with 10% aqueous citric acid solution
  5. dry with materialThe ether solution is dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to a white solid
  8. customThe solid is chromatographed on 230-400 mesh silica gel
  9. washeluting with dichloromethane

Sources & evidence

ORD record
ord-3d77ef596b344e4d8e98594216739e27
Source dataset
uspto-grants-1986_06
Patent number
US04596819

Reaction notes

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