Ethyl isocyanatoacetate → HCID 145857606, compound

HRID 2216117Notes

Reaction equation

HRID 2216117 reaction equation
[C:1]([O:5][C:6](=[O:40])[NH:7][C:8]([C:10]1[S:11][C:12]([S:38][CH3:39])=[C:13]([S:15]([C:18]2[CH:19]=[C:20]([C:24]3[C:29]([CH3:30])=[CH:28][CH:27]=[CH:26][C:25]=3[NH:31][C:32]([NH:34][CH2:35][CH2:36][NH2:37])=[O:33])[CH:21]=[CH:22][CH:23]=2)(=[O:17])=[O:16])[CH:14]=1)=[NH:9])([CH3:4])([CH3:3])[CH3:2].[N:41]([CH2:44][C:45]([O:47][CH2:48]C)=[O:46])=[C:42]=[O:43]>C(Cl)Cl>[CH3:48][O:47][C:45](=[O:46])[CH2:44][NH:41][C:42]([NH:37][CH2:36][CH2:35][NH:34][C:32]([NH:31][C:25]1[CH:26]=[CH:27][CH:28]=[C:29]([CH3:30])[C:24]=1[C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([S:15]([C:13]2[CH:14]=[C:10]([C:8]([NH:7][C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:40])=[NH:9])[S:11][C:12]=2[S:38][CH3:39])(=[O:16])=[O:17])[CH:19]=1)=[O:33])=[O:43]

Participants

4

Reactant 2

HCID 76283Ethyl isocyanatoacetateHCID 145857630HCID 145857630, compound

Product 1

HCID 145857606HCID 145857606, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of [(4-{2′-[3-(2-amino-ethyl)-ureido]-6′-methyl-biphenyl-3-sulfonyl}-5-methylsulfanyl-thiophen-2-yl)-imino-methyl]-carbamic acid tert-butyl ester ((Example 194: step a) 0.030 g, 0.050 mmol) in CH2Cl2 (10 mL) was treated with ethyl isocyanatoacetate (6.70 μL, 0.060 mmol) and stirred at room temperature 35 min. The reaction was diluted with CH2Cl2 and washed with water (1×15 mL). The organic layer was dried over MgSO4 and concentrated in vacuo to afford the product {3-[2-(3-{3′-[5-(tert-butoxycarbonylamino-imino-methyl)-2-methylsulfanyl-thiophene-3-sulfonyl]-6-methyl-biphenyl-2-yl}-ureido)-ethyl]-ureido}-acetic acid methyl ester (0.031 g, 86%) as an off-white solid. C32H40N6O8S3: 733.21 (M+1) found 732.90.

Workup

  1. washwashed with water (1×15 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-53e98a921a374875adf2a3bedc54a629
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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