Hydrochloric Acid → (2S,4S)-1-((S)-2-amino-2-cyclohexyl-acetyl)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-2-carboxylic acid benzyl ester hydrochloride

HRID 1481919Notes

Reaction equation

HRID 1481919 reaction equation
[CH2:1]([O:8][C:9]([C@@H:11]1[CH2:15][C@H:14]([NH:16][C:17]([O:19][CH2:20][CH:21]2[C:33]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:27]3[C:22]2=[CH:23][CH:24]=[CH:25][CH:26]=3)=[O:18])[CH2:13][N:12]1[C:34](=[O:50])[C@@H:35]([NH:42]C(OC(C)(C)C)=O)[CH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:51]>O1CCOCC1>[ClH:51].[CH2:1]([O:8][C:9]([C@@H:11]1[CH2:15][C@H:14]([NH:16][C:17]([O:19][CH2:20][CH:21]2[C:33]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:27]3[C:22]2=[CH:23][CH:24]=[CH:25][CH:26]=3)=[O:18])[CH2:13][N:12]1[C:34](=[O:50])[C@@H:35]([NH2:42])[CH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118677402(2S,4S)-1-((S)-2-tert-butoxycarbonylamino-2-cyclohexyl-acetyl)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-2-carboxylic acid benzyl ester

Product 1

HCID 90220202(2S,4S)-1-((S)-2-amino-2-cyclohexyl-acetyl)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-2-carboxylic acid benzyl ester hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(2S,4S)-1-((S)-2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-2-carboxylic acid benzyl ester (1.07 g, 1.77 mmol) was dissolved in 4 M HCl in 1,4-dioxane (6 mL) at 0° C. and stirred for 1 h, the cooling bath removed and the reaction stirred for 1 h. The mixture was concentrated and the residue triturated with diethyl ether to give (2S,4S)-1-((S)-2-amino-2-cyclohexyl-acetyl)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-2-carboxylic acid benzyl ester hydrochloride (0.97 g) as a light yellow solid which was used without further purification or characterization.

Workup

  1. customthe cooling bath removed
  2. stirringthe reaction stirred for 1 h
  3. concentrationThe mixture was concentrated
  4. customthe residue triturated with diethyl ether

Sources & evidence

ORD record
ord-6dcc42da817e49689529bea31bdc8c30
Source dataset
uspto-grants-2016_08
Patent number
US09409888B2

Reaction notes

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