Chlorotrimethylsilane → 2-((S)-2-{(R)-2-amino-2-[4-((S)-2,3-bis-trimethylsilanyloxy-propoxy)-phenyl]-acetylamino}-3-phenyl-propionylamino)-thiazole-4-carboxylic acid methyl ester

HRID 2222980Notes

Reaction equation

HRID 2222980 reaction equation
Cl[Si:2]([CH3:5])([CH3:4])[CH3:3].[CH3:6][O:7][C:8]([C:10]1[N:11]=[C:12]([NH:15][C:16](=[O:42])[C@@H:17]([NH:25][C:26](=[O:41])[C@H:27]([NH2:40])[C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][C@H:36]([OH:39])[CH2:37][OH:38])=[CH:30][CH:29]=2)[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[S:13][CH:14]=1)=[O:9].C(N(CC)CC)C>O1CCCC1.O>[CH3:6][O:7][C:8]([C:10]1[N:11]=[C:12]([NH:15][C:16](=[O:42])[C@@H:17]([NH:25][C:26](=[O:41])[C@H:27]([NH2:40])[C:28]2[CH:29]=[CH:30][C:31]([O:34][CH2:35][C@H:36]([O:39][Si:2]([CH3:5])([CH3:4])[CH3:3])[CH2:37][O:38][Si:2]([CH3:5])([CH3:4])[CH3:3])=[CH:32][CH:33]=2)[CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[S:13][CH:14]=1)=[O:9]

Participants

6

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 866040562-((S)-2-{(R)-2-amino-2-[4-((R)-2,3-dihydroxy-propoxy)-phenyl]-acetylamino}-3-phenyl-propionylamino)-thiazole-4-carboxylic acid methyl ester

Product 1

HCID 866040572-((S)-2-{(R)-2-amino-2-[4-((S)-2,3-bis-trimethylsilanyloxy-propoxy)-phenyl]-acetylamino}-3-phenyl-propionylamino)-thiazole-4-carboxylic acid methyl esterYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Chloro-trimethyl-silane (0.086 ml, 0.68 mmol) was added to 2-((S)-2-{(R)-2-amino-2-[4-((R)-2,3-dihydroxy-propoxy)-phenyl]-acetylamino}-3-phenyl-propionylamino)-thiazole-4-carboxylic acid methyl ester (120 mg, 0.23 mmol) in tetrahydrofuran (5 mL) containing triethylamine (0.10 ml, 0.73 mmol) at room temperature and stirred for 3 hours. The mixture was diluted with water and extracted with ethyl acetate. The organic extracts were washed with water, brine and dried over magnesium sulfate. Removal of solvents gave 2-((S)-2-{(R)-2-amino-2-[4-((S)-2,3-bis-trimethylsilanyloxy-propoxy)-phenyl]-acetylamino}-3-phenyl-propionylamino)-thiazole-4-carboxylic acid methyl ester as an oil (100 mg, 66%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic extracts were washed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. customRemoval of solvents

Sources & evidence

ORD record
ord-b1a9ae610c7941618d453980ca9dd388
Source dataset
uspto-grants-2008_05
Patent number
US07371869B2

Reaction notes

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