Chlorotrimethylsilane → HCID 59263942, compound

HRID 644977Notes

Reaction equation

HRID 644977 reaction equation
[OH:1][C:2]1[C:7]2[NH:8][C:9](=[O:11])[S:10][C:6]=2[C:5]([CH2:12][CH2:13][N:14]([CH2:25][CH2:26][NH:27][CH:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[C:15](=[O:24])[O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[Si](C)(C)C.Cl[C:47](=[O:71])[CH2:48][CH2:49][N:50]([CH2:61][CH2:62][C:63]1[CH:68]=[CH:67][C:66]([Cl:69])=[C:65]([Cl:70])[CH:64]=1)[C:51](=[O:60])[O:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1>ClCCl>[CH2:53]([O:52][C:51]([N:50]([CH2:61][CH2:62][C:63]1[CH:68]=[CH:67][C:66]([Cl:69])=[C:65]([Cl:70])[CH:64]=1)[CH2:49][CH2:48][C:47]([N:27]([CH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1)[CH2:26][CH2:25][N:14]([CH2:13][CH2:12][C:5]1[C:6]2[S:10][C:9](=[O:11])[NH:8][C:7]=2[C:2]([OH:1])=[CH:3][CH:4]=1)[C:15](=[O:24])[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:71])=[O:60])[C:54]1[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=1

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 59263843HCID 59263843, compoundHCID 59263932HCID 59263932, compound

Product 1

HCID 59263942HCID 59263942, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To an ice cooled suspension of benzyl 2-(4-hydroxy-2-oxo-2,3-dihydrobenzo[d]thiazol-7-yl)ethyl(2-(tetrahydro-2H-pyran-4-ylamino)ethyl)carbamate (2.5 g), as prepared as in Example 23 step i), in dichloromethane (40 mL) was added triethylamine (2.95 mL) followed by chlorotrimethylsilane (2.69 mL). The reaction was allowed to stir for 30 min before a solution of the acid chloride of step i) (2.198 g) in dichloromethane (20 mL) was added. The reaction was stirred for 2 h before the mixture was diluted with dichloromethane (200 mL), washed with water (150 mL) and saturated sodium hydrogen carbonate (150 mL), and the organic layer was dried over sodium sulphate, filtered and evaporated to afford crude product. This was purified by flash silica chromatography eluting with ethyl acetate. Pure fractions were evaporated to dryness to afford the sub-title product (3.10 g) as a off-white foam.

Workup

  1. additionwas added
  2. washwashed with water (150 mL) and saturated sodium hydrogen carbonate (150 mL)
  3. dry with materialthe organic layer was dried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customto afford crude product
  7. customThis was purified by flash silica chromatography
  8. washeluting with ethyl acetate
  9. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-2beb7e0db35042c2bae8143d100a4bf7
Source dataset
uspto-grants-2010_04
Patent number
US07700782B2

Reaction notes

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