Hydrochloric Acid → {(3S,5S)-1-((S)-2-Amino-2-cyclohexyl-acetyl)-5-[(R)-(1,2,3,4-tetrahydro-naphthalen-1-yl)carbamoyl]-pyrrolidin-3-yl}-carbamic acid 9H-fluoren-9-ylmethyl ester hydrochloride

HRID 1481913Notes

Reaction equation

HRID 1481913 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:53])[NH:17][C@H:18]3[CH2:22][C@@H:21]([C:23](=[O:35])[NH:24][C@H:25]4[C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[CH2:28][CH2:27][CH2:26]4)[N:20]([C:36](=[O:52])[C@@H:37]([NH:44]C(OC(C)(C)C)=O)[CH:38]4[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]4)[CH2:19]3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[ClH:54]>O1CCOCC1>[ClH:54].[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:53])[NH:17][C@H:18]3[CH2:22][C@@H:21]([C:23](=[O:35])[NH:24][C@H:25]4[C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[CH2:28][CH2:27][CH2:26]4)[N:20]([C:36](=[O:52])[C@@H:37]([NH2:44])[CH:38]4[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]4)[CH2:19]3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90220880{(3S,5S)-1-((S)-2-tert-butoxycarbonylamino-2-cyclohexyl-acetyl)-5-[(R)-(1,2,3,4-tetrahydro-naphthalen-1-yl)carbamoyl]-pyrrolidin-3-yl}-carbamic acid 9H-fluoren-9-ylmethyl ester2×

Product 1

HCID 118677398{(3S,5S)-1-((S)-2-Amino-2-cyclohexyl-acetyl)-5-[(R)-(1,2,3,4-tetrahydro-naphthalen-1-yl)carbamoyl]-pyrrolidin-3-yl}-carbamic acid 9H-fluoren-9-ylmethyl ester hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred solution of {(3S,5S)-1-((S)-2-tert-butoxycarbonylamino-2-cyclohexyl-acetyl)-5-[(R)-(1,2,3,4-tetrahydro-naphthalen-1-yl)carbamoyl]-pyrrolidin-3-yl}-carbamic acid 9H-fluoren-9-ylmethyl ester (Intermediate 23) (6.5 g, 9.03 mmol) in dioxane (25 mL) at 0° C. was added 4 M HCl in dioxane (50 mL) dropwise and then the cooling bath removed. After 6 h the mixture was evaporated and the residue was triturated with ether to provide the title compound (5.58 g) as a white solid. LC-MS: 621 (M+H).

Workup

  1. customthe cooling bath removed
  2. customAfter 6 h the mixture was evaporated
  3. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-deeba14f59614940a8bce34c9cbabf47
Source dataset
uspto-grants-2016_08
Patent number
US09409888B2

Reaction notes

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