Hydrochloric Acid → (2R)-2-amino-N-((2R)-3-(benzyloxy)-1-(2-methyl-1-oxo-4-phenyl-2,7-diazaspiro[4.5]decan-7-yl)-1-oxopropan-2-yl)-3-hydroxy-2-methylpropanamide

HRID 1036686Notes

Reaction equation

HRID 1036686 reaction equation
[CH3:1][C:2]([NH:45]C(=O)OC(C)(C)C)([CH2:36][O:37][Si](C)(C)C(C)(C)C)[C:3](=[O:35])[NH:4][C@@H:5]([C:15]([N:17]1[CH2:34][CH2:33][CH2:32][C:19]2([C:23](=[O:24])[N:22]([CH3:25])[CH2:21][CH:20]2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:18]1)=[O:16])[CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl.CCOCC.O>>[NH2:45][C@:2]([CH3:1])([CH2:36][OH:37])[C:3]([NH:4][C@H:5]([CH2:6][O:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:15]([N:17]1[CH2:34][CH2:33][CH2:32][C:19]2([C:23](=[O:24])[N:22]([CH3:25])[CH2:21][CH:20]2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:18]1)=[O:16])=[O:35]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3283Diethyl EtherHCID 86674096tert-butyl (4R)-7,10,10,11,11-pentamethyl-4-(2-methyl-1-oxo-4-phenyl-2,7-diazaspiro[4.5]decane-7-carbonyl)-6-oxo-1-phenyl-2,9-dioxa-5-aza-10-siladodecan-7-ylcarbamate2×

Product 1

HCID 71060302(2R)-2-amino-N-((2R)-3-(benzyloxy)-1-(2-methyl-1-oxo-4-phenyl-2,7-diazaspiro[4.5]decan-7-yl)-1-oxopropan-2-yl)-3-hydroxy-2-methylpropanamide

Procedure

A mixture comprising tert-butyl (4R)-7,10,10,11,11-pentamethyl-4-(2-methyl-1-oxo-4-phenyl-2,7-diazaspiro[4.5]decane-7-carbonyl)-6-oxo-1-phenyl-2,9-dioxa-5-aza-10-siladodecan-7-ylcarbamate (Intermediate from step 4) (140 mg, 0.190 mmol) and 2M HCl in Et2O (2.9 mL, 5.70 mmol) was treated with water (300 mg, 16.65 mmol) dropwise and stirred at room temperature for 2 hours. The reaction mixture was concentrated in vacuo. The resulting crude was dried in a vacuum oven for 24 hours at 50° C. to afford the title compound. No purification was performed on the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe resulting crude was dried in a vacuum oven for 24 hours at 50° C.

Sources & evidence

ORD record
ord-0d3dd6f0e76b4f7b9d214c7a06791f32
Source dataset
uspto-grants-2013_10
Patent number
US08546416B2

Reaction notes

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