Water → (2S)-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 1036687Notes

Reaction equation

HRID 1036687 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.CCOCC.O>C(Cl)Cl.Cl>[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

6

Reactant 3

HCID 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-ylcarbamate

Product 1

HCID 71060448(2S)-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

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

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 (150 mg, 0.204 mmol) in DCM (5 mL) and 2M HCl in Et2O (3.05 ml, 6.11 mmol) was treated with water (0.3 mL) dropwise at room temperature. The resulting colourless solution was stirred at room temperature for 2 hours. The reaction mixture was concentrated in vacuo. The resulting crude was dried in the vacuum oven at RT for 3 days to afford the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe resulting crude was dried in the vacuum oven at RT for 3 days

Sources & evidence

ORD record
ord-809a660ac02547dfa6c480540fe44958
Source dataset
uspto-grants-2013_10
Patent number
US08546416B2

Reaction notes

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