Ammonium Chloride → HCID 68942951, compound

HRID 532447Notes

Reaction equation

HRID 532447 reaction equation
[C:1]([Si:5]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)Cl)([CH3:4])([CH3:3])[CH3:2].[CH3:19][O:20][C:21]([C:23]1[S:24][C:25]([CH2:36][OH:37])=[CH:26][C:27]=1[NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[O:22].C(N(CC)C(C)C)(C)C.[Cl-].[NH4+]>ClCCl.CN(C)C1C=CN=CC=1>[CH3:19][O:20][C:21]([C:23]1[S:24][C:25]([CH2:36][O:37][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:26][C:27]=1[NH:28][C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:30])=[O:22]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 94078tert-ButyldiphenylchlorosilaneHCID 689407663-Tert-butoxycarbonylamino-5-hydroxymethyl-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 68942951HCID 68942951, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×

Procedure

tert-Butyldiphenylchlorosilane (1.7 g) dissolved in dichloromethane (5 mL) was added dropwise over the course of 10 min to a mixture of 3-tert-butoxycarbonylamino-5-hydroxymethylthiophene-2-carboxylic acid methyl ester (1.4 g), 4-dimethylaminopyridine (30.2 mg), N,N-diisopropylethylamine (1.3 mL) in dichloromethane (30 mL). The reaction mixture was then stirred at room temperature for 6 h. The mixture was mixed with dichloromethane and saturated ammonium chloride solution. The organic phase was washed with water, dried over sodium sulfate and concentrated. The product with the molecular weight of 525.74 (C28H35NO5SSi) was obtained in this way; MS (ESI): 426 (M-Boc+H+).

Workup

  1. washThe organic phase was washed with water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe product with the molecular weight of 525.74 (C28H35NO5SSi) was obtained in this way

Sources & evidence

ORD record
ord-881193c063dd430885815a2e38d811f1
Source dataset
uspto-grants-2014_10
Patent number
US08853208B2

Reaction notes

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